DE2405322A1 - Neue verfahren zur herstellung von benzylaminen - Google Patents
Neue verfahren zur herstellung von benzylaminenInfo
- Publication number
- DE2405322A1 DE2405322A1 DE19742405322 DE2405322A DE2405322A1 DE 2405322 A1 DE2405322 A1 DE 2405322A1 DE 19742405322 DE19742405322 DE 19742405322 DE 2405322 A DE2405322 A DE 2405322A DE 2405322 A1 DE2405322 A1 DE 2405322A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- temperatures
- carried out
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000003939 benzylamines Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000002253 acid Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 235000005985 organic acids Nutrition 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 112
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 66
- -1 cyano, carbamoyl Chemical group 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 3
- CHRAJVQLWOMYQI-SCZZXKLOSA-N (1s,5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical group C1NC[C@H]2CC[C@]1(C)C2(C)C CHRAJVQLWOMYQI-SCZZXKLOSA-N 0.000 claims description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical compound [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 2
- 230000020176 deacylation Effects 0.000 claims description 2
- 238000005947 deacylation reaction Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- 239000003434 antitussive agent Substances 0.000 abstract description 2
- 229940124584 antitussives Drugs 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 230000006181 N-acylation Effects 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 88
- 230000008018 melting Effects 0.000 description 88
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 9
- ZKNDQOZIXWLLJA-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoic acid Chemical compound C1CCCCC1N(CC)CC1=CC(C(O)=O)=CC(Br)=C1N ZKNDQOZIXWLLJA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- NSPDFNKTKFZSHA-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCOC(=O)C1=CC(Br)=C(N)C(CN(CC)CC)=C1 NSPDFNKTKFZSHA-UHFFFAOYSA-N 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- RWAOOOVHXZHLBK-UHFFFAOYSA-N 4-amino-3-bromo-5-(diethylaminomethyl)benzamide Chemical compound CCN(CC)CC1=CC(C(N)=O)=CC(Br)=C1N RWAOOOVHXZHLBK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- WEQBGTUFUFQQRR-UHFFFAOYSA-N (2-amino-3-bromo-5-ethoxycarbonylphenyl)methyl-trimethylazanium iodide Chemical compound [I-].NC1=C(C[N+](C)(C)C)C=C(C=C1Br)C(=O)OCC WEQBGTUFUFQQRR-UHFFFAOYSA-N 0.000 description 1
- JSTGQEVVENJCCT-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-[(dimethylamino)methyl]phenyl]ethanol Chemical compound CC(O)C1=CC(Br)=C(N)C(CN(C)C)=C1 JSTGQEVVENJCCT-UHFFFAOYSA-N 0.000 description 1
- YFRLDQCJQAHHTE-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-[(dimethylamino)methyl]phenyl]ethanone Chemical compound CN(C)CC1=CC(C(C)=O)=CC(Br)=C1N YFRLDQCJQAHHTE-UHFFFAOYSA-N 0.000 description 1
- GQQHWOKJSYGYEF-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]phenyl]ethanol Chemical compound C1CCCCC1N(CC)CC1=CC(C(C)O)=CC(Br)=C1N GQQHWOKJSYGYEF-UHFFFAOYSA-N 0.000 description 1
- QGUWFXIPCZDBMW-UHFFFAOYSA-N 2-bromo-6-[(dimethylamino)methyl]-4-fluoroaniline;hydrochloride Chemical compound Cl.CN(C)CC1=CC(F)=CC(Br)=C1N QGUWFXIPCZDBMW-UHFFFAOYSA-N 0.000 description 1
- XHEMKIDTRJZZBO-UHFFFAOYSA-N 2-bromo-6-[(dimethylamino)methyl]-4-methoxyaniline Chemical compound COC1=CC(Br)=C(N)C(CN(C)C)=C1 XHEMKIDTRJZZBO-UHFFFAOYSA-N 0.000 description 1
- BKARLTZHWNRCCF-UHFFFAOYSA-N 2-bromo-6-[[cyclohexyl(ethyl)amino]methyl]-4-methylaniline Chemical compound C1CCCCC1N(CC)CC1=CC(C)=CC(Br)=C1N BKARLTZHWNRCCF-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- NHWSJPAJJMPTIR-UHFFFAOYSA-N 3-(acetyloxymethyl)-4-amino-5-bromobenzoic acid Chemical compound C(C)(=O)OCC=1C=C(C(=O)O)C=C(C1N)Br NHWSJPAJJMPTIR-UHFFFAOYSA-N 0.000 description 1
- HTBBXSSHJGSFHO-UHFFFAOYSA-N 4-amino-3-[[cyclohexyl(methyl)amino]methyl]benzoic acid Chemical compound C1CCCCC1N(C)CC1=CC(C(O)=O)=CC=C1N HTBBXSSHJGSFHO-UHFFFAOYSA-N 0.000 description 1
- AVAXXWZAOLGRJG-UHFFFAOYSA-N 4-amino-3-bromo-5-(diethylaminomethyl)benzoic acid Chemical compound CCN(CC)CC1=CC(C(O)=O)=CC(Br)=C1N AVAXXWZAOLGRJG-UHFFFAOYSA-N 0.000 description 1
- LGUWYDNFNMYQLI-UHFFFAOYSA-N 4-amino-3-bromo-5-(diethylaminomethyl)benzonitrile Chemical compound CCN(CC)CC1=CC(C#N)=CC(Br)=C1N LGUWYDNFNMYQLI-UHFFFAOYSA-N 0.000 description 1
- KVIPSVUEZTXCDY-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzamide Chemical compound C1CCCCC1N(CC)CC1=CC(C(N)=O)=CC(Br)=C1N KVIPSVUEZTXCDY-UHFFFAOYSA-N 0.000 description 1
- VEPMMKKALPHWAG-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoic acid;hydrochloride Chemical compound Cl.C1CCCCC1N(CC)CC1=CC(C(O)=O)=CC(Br)=C1N VEPMMKKALPHWAG-UHFFFAOYSA-N 0.000 description 1
- JRGNEEGNXNZRSE-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzonitrile Chemical compound C1CCCCC1N(CC)CC1=CC(C#N)=CC(Br)=C1N JRGNEEGNXNZRSE-UHFFFAOYSA-N 0.000 description 1
- ZJMVCJABJWWINR-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(methyl)amino]methyl]benzoic acid Chemical compound C1CCCCC1N(C)CC1=CC(C(O)=O)=CC(Br)=C1N ZJMVCJABJWWINR-UHFFFAOYSA-N 0.000 description 1
- DSJQMDTYLYNJIO-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(methyl)amino]methyl]benzonitrile hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(C#N)=CC(Br)=C1N DSJQMDTYLYNJIO-UHFFFAOYSA-N 0.000 description 1
- SNMVVJCMCJFRAU-UHFFFAOYSA-N 4-amino-3-bromo-5-formylbenzoic acid Chemical compound NC1=C(C=O)C=C(C=C1Br)C(=O)O SNMVVJCMCJFRAU-UHFFFAOYSA-N 0.000 description 1
- DRERNFYGACDGIW-UHFFFAOYSA-N 4-bromo-2-[(dimethylamino)methyl]-6-fluoroaniline;hydrochloride Chemical compound Cl.CN(C)CC1=CC(Br)=CC(F)=C1N DRERNFYGACDGIW-UHFFFAOYSA-N 0.000 description 1
- VKKBXHJUULMKQC-UHFFFAOYSA-N 4-bromo-2-[[cyclohexyl(ethyl)amino]methyl]-6-fluoroaniline Chemical compound C1CCCCC1N(CC)CC1=CC(Br)=CC(F)=C1N VKKBXHJUULMKQC-UHFFFAOYSA-N 0.000 description 1
- AGSLHDHPEVXMOP-UHFFFAOYSA-N 4-bromo-2-[[cyclohexyl(methyl)amino]methyl]-6-fluoroaniline Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(F)=C1N AGSLHDHPEVXMOP-UHFFFAOYSA-N 0.000 description 1
- JWWRXURRNIISQC-UHFFFAOYSA-N 4-bromo-5-tert-butyl-2-(morpholin-4-ylmethyl)aniline;dihydrochloride Chemical compound Cl.Cl.C1=C(Br)C(C(C)(C)C)=CC(N)=C1CN1CCOCC1 JWWRXURRNIISQC-UHFFFAOYSA-N 0.000 description 1
- XTTHXAIYLCTVEE-UHFFFAOYSA-N 4-methoxy-2-(piperidin-1-ylmethyl)aniline Chemical compound COC1=CC=C(N)C(CN2CCCCC2)=C1 XTTHXAIYLCTVEE-UHFFFAOYSA-N 0.000 description 1
- XAZNOOMRYLFDQO-UHFFFAOYSA-N 4h-3,1-benzoxazine Chemical compound C1=CC=C2COC=NC2=C1 XAZNOOMRYLFDQO-UHFFFAOYSA-N 0.000 description 1
- AENLNOKZFAXBIE-UHFFFAOYSA-N C(C)N(C1CCCCC1)CC1=C(C(=CC(=C1)F)Br)N.Cl Chemical compound C(C)N(C1CCCCC1)CC1=C(C(=CC(=C1)F)Br)N.Cl AENLNOKZFAXBIE-UHFFFAOYSA-N 0.000 description 1
- CMWHCQNPASVLPA-UHFFFAOYSA-N C1(=CC=CC=C1)OCC1=C(C(=CC(=C1)C(=O)OCC)Br)N Chemical compound C1(=CC=CC=C1)OCC1=C(C(=CC(=C1)C(=O)OCC)Br)N CMWHCQNPASVLPA-UHFFFAOYSA-N 0.000 description 1
- JLTCBUKSOIBLIH-UHFFFAOYSA-N CCOC([N+](C)(C)OC1=CC=CC=C1)OC Chemical compound CCOC([N+](C)(C)OC1=CC=CC=C1)OC JLTCBUKSOIBLIH-UHFFFAOYSA-N 0.000 description 1
- QRFCUAOQJNKWEI-HDJSIYSDSA-N CN([C@@H]1CC[C@@H](O)CC1)CC1=CC(Br)=CC(C)=C1N Chemical compound CN([C@@H]1CC[C@@H](O)CC1)CC1=CC(Br)=CC(C)=C1N QRFCUAOQJNKWEI-HDJSIYSDSA-N 0.000 description 1
- WXEBJUDINPXVMO-WKILWMFISA-N CN([C@@H]1CC[C@@H](O)CC1)CC1=CC(Br)=CC(C)=C1NC(C)=O Chemical compound CN([C@@H]1CC[C@@H](O)CC1)CC1=CC(Br)=CC(C)=C1NC(C)=O WXEBJUDINPXVMO-WKILWMFISA-N 0.000 description 1
- QGFUOGACUXEJFR-UHFFFAOYSA-N Cl.C(C)(=O)C=1C=C(C(=C(CN(C)C2CCCCC2)C1)N)Br Chemical compound Cl.C(C)(=O)C=1C=C(C(=C(CN(C)C2CCCCC2)C1)N)Br QGFUOGACUXEJFR-UHFFFAOYSA-N 0.000 description 1
- AAGJGGVNWYMOGY-UHFFFAOYSA-N Cl.C(C)(=O)NC1=C(CN(C)C)C=CC=C1C Chemical compound Cl.C(C)(=O)NC1=C(CN(C)C)C=CC=C1C AAGJGGVNWYMOGY-UHFFFAOYSA-N 0.000 description 1
- FZGJPNRYVLGNRT-UHFFFAOYSA-N Cl.C(C)(=O)NC1=C(CN(C)C2CCCCC2)C=C(C=C1C(C)(C)C)Br Chemical compound Cl.C(C)(=O)NC1=C(CN(C)C2CCCCC2)C=C(C=C1C(C)(C)C)Br FZGJPNRYVLGNRT-UHFFFAOYSA-N 0.000 description 1
- JTVXPNOHJXRDKQ-UHFFFAOYSA-N Cl.C(C)(=O)NC1=C(CN(CC)CC)C=C(C=C1C)Br Chemical compound Cl.C(C)(=O)NC1=C(CN(CC)CC)C=C(C=C1C)Br JTVXPNOHJXRDKQ-UHFFFAOYSA-N 0.000 description 1
- AVCNJNLFULCUQI-UHFFFAOYSA-N Cl.Cl.BrC1=CC(=C(N)C(=C1)CN1CCOCC1)CN1CCOCC1 Chemical compound Cl.Cl.BrC1=CC(=C(N)C(=C1)CN1CCOCC1)CN1CCOCC1 AVCNJNLFULCUQI-UHFFFAOYSA-N 0.000 description 1
- WIQSABGIALNLBX-UHFFFAOYSA-N Cl.Cl.C(C)(=O)NC1=C(CN2CCN(CC2)C)C=C(C(=C1)C(C)(C)C)Br Chemical compound Cl.Cl.C(C)(=O)NC1=C(CN2CCN(CC2)C)C=C(C(=C1)C(C)(C)C)Br WIQSABGIALNLBX-UHFFFAOYSA-N 0.000 description 1
- MGWXQSJNROEYBO-UHFFFAOYSA-N Cl.Cl.N1(CCCC1)CCC(=O)NC1=CC=CC=C1 Chemical compound Cl.Cl.N1(CCCC1)CCC(=O)NC1=CC=CC=C1 MGWXQSJNROEYBO-UHFFFAOYSA-N 0.000 description 1
- RJCANNLMBYCJRX-UHFFFAOYSA-N Cl.Cl.N1(CCCCC1)CCC(=O)NC1=CC=CC=C1 Chemical compound Cl.Cl.N1(CCCCC1)CCC(=O)NC1=CC=CC=C1 RJCANNLMBYCJRX-UHFFFAOYSA-N 0.000 description 1
- REGVVKCSQCIWCZ-UHFFFAOYSA-N Cl.Cl.NC1=C(CN(C)C)C=C(C=C1CN(C)C)Br Chemical compound Cl.Cl.NC1=C(CN(C)C)C=C(C=C1CN(C)C)Br REGVVKCSQCIWCZ-UHFFFAOYSA-N 0.000 description 1
- GWWCVIHLIUAHBZ-UHFFFAOYSA-N Cl.Cl.NC1=C(CN2CCCCC2)C=C(C=C1C)Br Chemical compound Cl.Cl.NC1=C(CN2CCCCC2)C=C(C=C1C)Br GWWCVIHLIUAHBZ-UHFFFAOYSA-N 0.000 description 1
- NQFYIGMNLLHATJ-UHFFFAOYSA-N Cl.NC1=C(CN(C)C2CCCCC2)C=C(C=C1C)Br Chemical compound Cl.NC1=C(CN(C)C2CCCCC2)C=C(C=C1C)Br NQFYIGMNLLHATJ-UHFFFAOYSA-N 0.000 description 1
- RXCYUVJNTWKCJD-UHFFFAOYSA-N Cl.NC1=C(CN(CC)CC)C=C(C=C1)C(=O)O Chemical compound Cl.NC1=C(CN(CC)CC)C=C(C=C1)C(=O)O RXCYUVJNTWKCJD-UHFFFAOYSA-N 0.000 description 1
- VGCMYSCRYWFXMR-UHFFFAOYSA-N Cl.NC1=C(CN(CC)CC)C=C(C=C1Br)F Chemical compound Cl.NC1=C(CN(CC)CC)C=C(C=C1Br)F VGCMYSCRYWFXMR-UHFFFAOYSA-N 0.000 description 1
- MWDCERNACCBGKF-UHFFFAOYSA-N Cl.NC1=C(CN(CC)CC)C=C(C=C1C(F)(F)F)Br Chemical compound Cl.NC1=C(CN(CC)CC)C=C(C=C1C(F)(F)F)Br MWDCERNACCBGKF-UHFFFAOYSA-N 0.000 description 1
- NZELMEUSWDORQD-UHFFFAOYSA-N Cl.NC1=C(CN2CCOCC2)C=C(C=C1Br)F Chemical compound Cl.NC1=C(CN2CCOCC2)C=C(C=C1Br)F NZELMEUSWDORQD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- BVMHFVFQQTUZHB-UHFFFAOYSA-N NC1=C(COCC)C=C(C=C1Br)C(=O)O Chemical compound NC1=C(COCC)C=C(C=C1Br)C(=O)O BVMHFVFQQTUZHB-UHFFFAOYSA-N 0.000 description 1
- XAGODGADOODBPF-XYPYZODXSA-N NC1=C(F)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 Chemical compound NC1=C(F)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 XAGODGADOODBPF-XYPYZODXSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- QPYBBWAWQVKQPJ-UHFFFAOYSA-N [I-].NC1=C(C[N+](CC)(CC)C)C=C(C=C1Br)C(=O)O Chemical compound [I-].NC1=C(C[N+](CC)(CC)C)C=C(C=C1Br)C(=O)O QPYBBWAWQVKQPJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- WIDZBVDLPJOKQV-UHFFFAOYSA-M ethyl 1-benzylpyridin-1-ium-2-carboxylate bromide Chemical compound [Br-].CCOC(=O)C1=CC=CC=[N+]1CC1=CC=CC=C1 WIDZBVDLPJOKQV-UHFFFAOYSA-M 0.000 description 1
- ZNNCWBMLQGWBNM-UHFFFAOYSA-N ethyl 3-(acetyloxymethyl)-4-amino-5-bromobenzoate Chemical compound C(C)(=O)OCC=1C=C(C(=O)OCC)C=C(C1N)Br ZNNCWBMLQGWBNM-UHFFFAOYSA-N 0.000 description 1
- UCEAARZZTMDNRF-UHFFFAOYSA-N ethyl 3-bromo-5-(diethylaminomethyl)-4-nitrobenzoate Chemical compound BrC=1C(=C(CN(CC)CC)C=C(C1)C(=O)OCC)[N+](=O)[O-] UCEAARZZTMDNRF-UHFFFAOYSA-N 0.000 description 1
- DBDMMDVFFIVMQM-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC(Br)=C(N)C(CN(CC)CC)=C1 DBDMMDVFFIVMQM-UHFFFAOYSA-N 0.000 description 1
- ITFMBYIPBJLLSV-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-(ethylaminomethyl)benzoate Chemical compound CCNCC1=CC(C(=O)OCC)=CC(Br)=C1N ITFMBYIPBJLLSV-UHFFFAOYSA-N 0.000 description 1
- SBKMMVQOIMHOOL-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-formylbenzoate Chemical compound NC1=C(C=O)C=C(C=C1Br)C(=O)OCC SBKMMVQOIMHOOL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JXNFRQHDYJJJNT-UHFFFAOYSA-N methyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OC)=CC(Br)=C1N JXNFRQHDYJJJNT-UHFFFAOYSA-N 0.000 description 1
- RICCWWXVEGUBJX-UHFFFAOYSA-N n-[4-acetyl-2-(diethylaminomethyl)phenyl]acetamide Chemical compound CCN(CC)CC1=CC(C(C)=O)=CC=C1NC(C)=O RICCWWXVEGUBJX-UHFFFAOYSA-N 0.000 description 1
- GGNKWYAPZNJEQI-UHFFFAOYSA-N n-[4-bromo-2,6-bis[[cyclohexyl(methyl)amino]methyl]phenyl]acetamide Chemical compound C1CCCCC1N(C)CC(C=1NC(C)=O)=CC(Br)=CC=1CN(C)C1CCCCC1 GGNKWYAPZNJEQI-UHFFFAOYSA-N 0.000 description 1
- HOWKWDBLKPDNPQ-UHFFFAOYSA-N n-[4-bromo-2-[[cyclohexyl(methyl)amino]methyl]-6-methylphenyl]acetamide Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(C)=C1NC(C)=O HOWKWDBLKPDNPQ-UHFFFAOYSA-N 0.000 description 1
- DTZVRIVVGLLEPI-UHFFFAOYSA-N n-[4-bromo-2-methyl-6-(morpholin-4-ylmethyl)phenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=C(Br)C=C1CN1CCOCC1 DTZVRIVVGLLEPI-UHFFFAOYSA-N 0.000 description 1
- KAWLNJQDCSVYKJ-UHFFFAOYSA-N n-[4-bromo-2-methyl-6-(piperidin-1-ylmethyl)phenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=C(Br)C=C1CN1CCCCC1 KAWLNJQDCSVYKJ-UHFFFAOYSA-N 0.000 description 1
- KYKYTBRJTMKMBY-UHFFFAOYSA-N n-[4-bromo-2-methyl-6-(pyrrolidin-1-ylmethyl)phenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=C(Br)C=C1CN1CCCC1 KYKYTBRJTMKMBY-UHFFFAOYSA-N 0.000 description 1
- LSZODIVUHOJJHS-UHFFFAOYSA-N n-[4-bromo-5-tert-butyl-2-(diethylaminomethyl)phenyl]acetamide Chemical compound CCN(CC)CC1=CC(Br)=C(C(C)(C)C)C=C1NC(C)=O LSZODIVUHOJJHS-UHFFFAOYSA-N 0.000 description 1
- NFXIEXIAOHHDTH-UHFFFAOYSA-N n-[4-bromo-5-tert-butyl-2-(piperidin-1-ylmethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(C(C)(C)C)=C(Br)C=C1CN1CCCCC1 NFXIEXIAOHHDTH-UHFFFAOYSA-N 0.000 description 1
- PAYDUUFACYKFRI-UHFFFAOYSA-N n-bis[cyclohexyl(methyl)amino]phosphoryl-n-methylcyclohexanamine Chemical compound C1CCCCC1N(C)P(=O)(N(C)C1CCCCC1)N(C)C1CCCCC1 PAYDUUFACYKFRI-UHFFFAOYSA-N 0.000 description 1
- NVEYVSRXOFPIRE-UHFFFAOYSA-N n-cyclohexyl-n-methylacetamide Chemical compound CC(=O)N(C)C1CCCCC1 NVEYVSRXOFPIRE-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008030 superplasticizer Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (62)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405322 DE2405322A1 (de) | 1974-02-05 | 1974-02-05 | Neue verfahren zur herstellung von benzylaminen |
| AT202374A AT332375B (de) | 1973-04-13 | 1974-03-12 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| ES424432A ES424432A1 (es) | 1973-04-13 | 1974-03-20 | Procedimiento para la preparacion de nuevas bencilaminas. |
| SU2012364A SU517250A3 (ru) | 1973-04-13 | 1974-04-04 | Способ получени производных бензиламина или их солей |
| RO7482360A RO70260A (ro) | 1973-04-13 | 1974-04-09 | Procedeu pentru prepararea unor benzilamine |
| CH528877A CH609035A5 (en) | 1974-02-05 | 1974-04-09 | Process for the preparation of novel benzylamines |
| CH529277A CH609329A5 (en) | 1974-02-05 | 1974-04-09 | Process for the preparation of novel benzylamines |
| CH528677A CH609041A5 (en) | 1973-04-13 | 1974-04-09 | Process for the preparation of novel benzylamines |
| CH529477A CH592609A5 (enrdf_load_stackoverflow) | 1974-02-05 | 1974-04-09 | |
| CH493174A CH609327A5 (en) | 1973-04-13 | 1974-04-09 | Process for the preparation of novel benzylamines |
| CH529077A CH609037A5 (en) | 1974-02-05 | 1974-04-09 | Process for the preparation of novel benzylamines |
| RO7478362A RO69152A (ro) | 1973-04-13 | 1974-04-09 | Procedeu pentru prepararea unor benzilamine |
| RO82361A RO69291B (ro) | 1973-04-13 | 1974-04-09 | Procedeu pentru prepararea unor benzilamine |
| CH528977A CH609036A5 (en) | 1974-02-05 | 1974-04-09 | Process for the preparation of novel benzylamines |
| CH529177A CH609038A5 (en) | 1974-02-05 | 1974-04-09 | Process for the preparation of novel benzylamines |
| HUTO959A HU167971B (en) | 1973-04-13 | 1974-04-10 | Process for producing new substituted benzylamines |
| JP4085974A JPS5634582B2 (enrdf_load_stackoverflow) | 1973-04-13 | 1974-04-10 | |
| NO741350A NO138250C (no) | 1973-04-13 | 1974-04-10 | Analogifremgangsmaate for fremstilling av farmakologisk aktive benzylaminer |
| BG026374A BG25787A3 (en) | 1973-04-13 | 1974-04-11 | A method of obtaining benzylamines |
| GB1625474A GB1469187A (en) | 1973-04-13 | 1974-04-11 | Substituted aminobenzylamines |
| AU67783/74A AU489908B2 (en) | 1973-04-13 | 1974-04-11 | Benzylamines |
| CA197,507A CA1011748A (en) | 1973-04-13 | 1974-04-11 | Benzylamines |
| CS742629A CS188920B2 (en) | 1973-04-13 | 1974-04-11 | Method of producing novel aminobenzylamines |
| IE790/74A IE40146B1 (en) | 1973-04-13 | 1974-04-11 | Substituted aminobenzylamines |
| SE7405020A SE411749B (sv) | 1973-04-13 | 1974-04-11 | Forfarande for framstellning av nya bensylaminer |
| NL7404965A NL7404965A (enrdf_load_stackoverflow) | 1973-04-13 | 1974-04-11 | |
| DD177856A DD113748A5 (enrdf_load_stackoverflow) | 1973-04-13 | 1974-04-11 | |
| PL18143174A PL96532B1 (pl) | 1974-02-05 | 1974-04-12 | Sposob wytwarzania nowych benzyloamin |
| IL44623A IL44623A (en) | 1973-04-13 | 1974-04-12 | Benzylamines their preparation and pharmaceutical compositions containing them |
| PL18143674A PL94232B1 (enrdf_load_stackoverflow) | 1974-02-05 | 1974-04-12 | |
| PL18143474A PL95668B1 (pl) | 1974-02-05 | 1974-04-12 | Sposob wytwarzania nowych benzyloamin |
| FR7413024A FR2225165B1 (enrdf_load_stackoverflow) | 1973-04-13 | 1974-04-12 | |
| PL18143574A PL94231B1 (enrdf_load_stackoverflow) | 1974-02-05 | 1974-04-12 | |
| PL1974170327A PL89811B1 (enrdf_load_stackoverflow) | 1973-04-13 | 1974-04-12 | |
| PL18143374A PL96785B1 (pl) | 1974-02-05 | 1974-04-12 | Sposob wytwarzania nowych benzyloamin |
| PL18143774A PL94234B1 (enrdf_load_stackoverflow) | 1974-02-05 | 1974-04-12 | |
| PL1974181429A PL102867B1 (pl) | 1973-04-13 | 1974-04-12 | Sposob wytwarzania nowych benzyloamin |
| PL18143274A PL94279B1 (enrdf_load_stackoverflow) | 1974-02-05 | 1974-04-12 | |
| ES433895A ES433895A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433900A ES433900A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433897A ES433897A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433899A ES433899A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433893A ES433893A1 (es) | 1973-04-13 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433898A ES433898A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433901A ES433901A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| ES433896A ES433896A1 (es) | 1974-02-05 | 1975-01-17 | Procedimiento para la preparacion de nuevas bencilaminas. |
| SU752101062A SU640657A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU7502101047A SU575021A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101064A SU528866A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101049A SU520035A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензаламина или их солей |
| SU2101046A SU521836A3 (ru) | 1973-04-13 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101063A SU521838A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101058A SU523634A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101060A SU527134A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| AT502275A AT342027B (de) | 1973-04-13 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzoesauren sowie deren saureadditionssalzen |
| AT502875A AT331216B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| AT503075A AT340399B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung neuer aminobenzoesaurealkylester und deren saureadditionssalze |
| AT502975A AT331217B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| AT502475A AT331213B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| AT502575A AT331214B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| AT502775A AT331215B (de) | 1974-02-05 | 1975-07-01 | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
| CH529377A CH617662A5 (en) | 1974-02-05 | 1977-04-28 | Process for the preparation of novel benzylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405322 DE2405322A1 (de) | 1974-02-05 | 1974-02-05 | Neue verfahren zur herstellung von benzylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2405322A1 true DE2405322A1 (de) | 1975-09-04 |
Family
ID=5906596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742405322 Pending DE2405322A1 (de) | 1973-04-13 | 1974-02-05 | Neue verfahren zur herstellung von benzylaminen |
Country Status (5)
| Country | Link |
|---|---|
| CH (7) | CH592609A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2405322A1 (enrdf_load_stackoverflow) |
| ES (1) | ES433900A1 (enrdf_load_stackoverflow) |
| PL (7) | PL96785B1 (enrdf_load_stackoverflow) |
| SU (7) | SU527134A3 (enrdf_load_stackoverflow) |
-
1974
- 1974-02-05 DE DE19742405322 patent/DE2405322A1/de active Pending
- 1974-04-09 CH CH529477A patent/CH592609A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529277A patent/CH609329A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH528977A patent/CH609036A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH528877A patent/CH609035A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529077A patent/CH609037A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529177A patent/CH609038A5/xx not_active IP Right Cessation
- 1974-04-12 PL PL18143374A patent/PL96785B1/pl unknown
- 1974-04-12 PL PL18143574A patent/PL94231B1/pl unknown
- 1974-04-12 PL PL18143174A patent/PL96532B1/pl unknown
- 1974-04-12 PL PL18143774A patent/PL94234B1/pl unknown
- 1974-04-12 PL PL18143274A patent/PL94279B1/pl unknown
- 1974-04-12 PL PL18143474A patent/PL95668B1/pl unknown
- 1974-04-12 PL PL18143674A patent/PL94232B1/pl unknown
-
1975
- 1975-01-17 ES ES433900A patent/ES433900A1/es not_active Expired
- 1975-01-30 SU SU2101060A patent/SU527134A3/ru active
- 1975-01-30 SU SU752101062A patent/SU640657A3/ru active
- 1975-01-30 SU SU2101064A patent/SU528866A3/ru active
- 1975-01-30 SU SU2101058A patent/SU523634A3/ru active
- 1975-01-30 SU SU2101063A patent/SU521838A3/ru active
- 1975-01-30 SU SU7502101047A patent/SU575021A3/ru active
- 1975-01-30 SU SU2101049A patent/SU520035A3/ru active
-
1977
- 1977-04-28 CH CH529377A patent/CH617662A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SU521838A3 (ru) | 1976-07-15 |
| SU520035A3 (ru) | 1976-06-30 |
| SU527134A3 (ru) | 1976-08-30 |
| PL95668B1 (pl) | 1977-11-30 |
| CH609329A5 (en) | 1979-02-28 |
| SU528866A3 (ru) | 1976-09-15 |
| CH592609A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| CH609038A5 (en) | 1979-02-15 |
| PL94232B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| SU575021A3 (ru) | 1977-09-30 |
| CH609036A5 (en) | 1979-02-15 |
| PL94231B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| CH609035A5 (en) | 1979-02-15 |
| PL94279B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| PL96532B1 (pl) | 1977-12-31 |
| PL96785B1 (pl) | 1978-01-31 |
| ES433900A1 (es) | 1976-12-01 |
| CH609037A5 (en) | 1979-02-15 |
| CH617662A5 (en) | 1980-06-13 |
| PL94234B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| SU523634A3 (ru) | 1976-07-30 |
| SU640657A3 (ru) | 1978-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2243961C2 (enrdf_load_stackoverflow) | ||
| EP0064685A1 (de) | Dibenzo(de,g)chinolin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE3324532A1 (de) | Verfahren zur herstellung von (plus-minus)4oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)-isochinolinderivaten | |
| DE60104704T2 (de) | Verfahren zur herstellung einer substituierten imidazopyridinverbindung | |
| DE2008692A1 (de) | Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue Verbindungen | |
| DE3871591T2 (de) | Verfahren zur herstellung von 1-propargyl-2,4-dioxoimidazolidin. | |
| DE2405322A1 (de) | Neue verfahren zur herstellung von benzylaminen | |
| CH638516A5 (en) | Process for preparing substituted aminoquinazoline derivatives | |
| WO1990012796A1 (de) | 8β-SUBSTITUIERTE ERGOLINE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG | |
| DE2653251A1 (de) | Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung | |
| DE3815046A1 (de) | 3-chlor-2-methylphenethylaminoderivate | |
| AT376417B (de) | Verfahren zur herstellung von phenylaethanolaminen und ihren salzen | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| DE1620128B2 (de) | N-aminoalkyl-2-phenoxy-2-phenylacetamide, deren saeureadditionssalze, sowie verfahren zu ihrer herstellung | |
| AT286288B (de) | Verfahren zur Herstellung neuer Indolderivate | |
| AT347473B (de) | Verfahren zur herstellung von neuen morpholinverbindungen und deren nicht-toxischen salzen | |
| AT359210B (de) | Verfahren zur herstellung von desoxyvincamin- amiden | |
| AT351528B (de) | Verfahren zur herstellung von neuen indazol- derivaten | |
| AT210421B (de) | Verfahren zur Herstellung von neuen, esterartigen 4-Hydroxy-piperidin-Derivaten | |
| AT218526B (de) | Verfahren zur Herstellung von neuen Phenthiazinderivaten | |
| AT273972B (de) | Verfahren zur Herstellung von neuen 1-(2-Aminophenyl)-1,2,3,4-tetrahydroisochinolinen sowie von deren Salzen | |
| CH605617A5 (en) | 2-Aminobenzylamine derivs prepn. | |
| AT211313B (de) | Verfahren zur Herstellung von neuen, substituierten Piperidinverbindungen | |
| EP0090769A2 (de) | Verfahren zur Herstellung von 1,2,5,6-Tetrahydro-4H-pyrrolo(3,2,1-ij)-chinolin-4-on und neue 5-Halogen-1,2,3-(1,2-dihydropyrrolo)-4-chinolone als Zwischenprodukte zur Durchführung des Verfahrens | |
| DE1620556C (de) | 1 Cyclohexylbarbitursaure derivate |