SU523634A3 - Способ получени производных бензиламина или их солей - Google Patents
Способ получени производных бензиламина или их солейInfo
- Publication number
- SU523634A3 SU523634A3 SU2101058A SU2101058A SU523634A3 SU 523634 A3 SU523634 A3 SU 523634A3 SU 2101058 A SU2101058 A SU 2101058A SU 2101058 A SU2101058 A SU 2101058A SU 523634 A3 SU523634 A3 SU 523634A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bromo
- amino
- hydrochloride
- decomp
- cyclohexyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 150000003939 benzylamines Chemical class 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 amine hydrochloride Chemical class 0.000 claims description 15
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 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 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229960004011 methenamine Drugs 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 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
- UETQVDZZPKAQIC-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl UETQVDZZPKAQIC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 3
- MRDXZDQDUZPTTJ-UHFFFAOYSA-N (3-fluorophenyl)methyl-methylazanium;chloride Chemical compound Cl.CNCC1=CC=CC(F)=C1 MRDXZDQDUZPTTJ-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 claims 1
- KWOOYVLMIMRTBO-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-methoxyaniline Chemical compound COC1=CC=C(N)C(CN(C)C)=C1 KWOOYVLMIMRTBO-UHFFFAOYSA-N 0.000 claims 1
- WPMYNYLCZCLLJF-UHFFFAOYSA-N 2-bromo-4-fluoro-6-(morpholin-4-ylmethyl)aniline Chemical group NC1=C(Br)C=C(F)C=C1CN1CCOCC1 WPMYNYLCZCLLJF-UHFFFAOYSA-N 0.000 claims 1
- NMOREOJGPXZMKC-UHFFFAOYSA-N 4-bromo-2-(diethylaminomethyl)-6-methylaniline;hydrochloride Chemical compound Cl.CCN(CC)CC1=CC(Br)=CC(C)=C1N NMOREOJGPXZMKC-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
- CBSOFSBFHDQRLV-UHFFFAOYSA-N N-methylbenzylamine hydrochloride Chemical compound [Cl-].C[NH2+]CC1=CC=CC=C1 CBSOFSBFHDQRLV-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-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
- 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FGCIWARUTHVIQO-UHFFFAOYSA-N N-phenylacetamide dihydrochloride Chemical compound Cl.Cl.C(C)(=O)NC1=CC=CC=C1 FGCIWARUTHVIQO-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- BBRMJFQSFXHBOW-UHFFFAOYSA-N ethyl 4-acetamido-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCOC(=O)C1=CC(Br)=C(NC(C)=O)C(CN(CC)CC)=C1 BBRMJFQSFXHBOW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GVWTYLBUUFELJD-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-[[cyclohexyl(methyl)amino]methyl]benzoate Chemical compound CCOC(=O)C1=CC(Br)=C(N)C(CN(C)C2CCCCC2)=C1 GVWTYLBUUFELJD-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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004310 lactic acid 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IIEWBAQJZGHTKE-UHFFFAOYSA-N n-[2-bromo-6-(diethylaminomethyl)-4-methylphenyl]acetamide Chemical compound CCN(CC)CC1=CC(C)=CC(Br)=C1NC(C)=O IIEWBAQJZGHTKE-UHFFFAOYSA-N 0.000 description 1
- JDWBYGILPVUOSO-UHFFFAOYSA-N n-[2-bromo-6-(diethylaminomethyl)-4-methylphenyl]acetamide;hydrochloride Chemical compound Cl.CCN(CC)CC1=CC(C)=CC(Br)=C1NC(C)=O JDWBYGILPVUOSO-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
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011975 tartaric acid Substances 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)
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 |
|---|---|
| SU523634A3 true SU523634A3 (ru) | 1976-07-30 |
Family
ID=5906596
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| SU752101062A SU640657A3 (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 |
| SU7502101047A SU575021A3 (ru) | 1974-02-05 | 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 |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2101060A SU527134A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU752101062A SU640657A3 (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 |
| SU7502101047A SU575021A3 (ru) | 1974-02-05 | 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 |
Country Status (5)
| Country | Link |
|---|---|
| CH (7) | CH609329A5 (enExample) |
| DE (1) | DE2405322A1 (enExample) |
| ES (1) | ES433900A1 (enExample) |
| PL (7) | PL94232B1 (enExample) |
| SU (7) | SU523634A3 (enExample) |
-
1974
- 1974-02-05 DE DE19742405322 patent/DE2405322A1/de active Pending
- 1974-04-09 CH CH529277A patent/CH609329A5/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
- 1974-04-09 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 CH529477A patent/CH592609A5/xx not_active IP Right Cessation
- 1974-04-12 PL PL18143674A patent/PL94232B1/pl unknown
- 1974-04-12 PL PL18143174A patent/PL96532B1/pl unknown
- 1974-04-12 PL PL18143574A patent/PL94231B1/pl unknown
- 1974-04-12 PL PL18143374A patent/PL96785B1/pl unknown
- 1974-04-12 PL PL18143474A patent/PL95668B1/pl unknown
- 1974-04-12 PL PL18143274A patent/PL94279B1/pl unknown
- 1974-04-12 PL PL18143774A patent/PL94234B1/pl unknown
-
1975
- 1975-01-17 ES ES433900A patent/ES433900A1/es not_active Expired
- 1975-01-30 SU SU2101058A patent/SU523634A3/ru active
- 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 SU2101049A patent/SU520035A3/ru active
- 1975-01-30 SU SU7502101047A patent/SU575021A3/ru active
- 1975-01-30 SU SU2101063A patent/SU521838A3/ru active
-
1977
- 1977-04-28 CH CH529377A patent/CH617662A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SU640657A3 (ru) | 1978-12-30 |
| CH609038A5 (en) | 1979-02-15 |
| SU520035A3 (ru) | 1976-06-30 |
| CH617662A5 (en) | 1980-06-13 |
| ES433900A1 (es) | 1976-12-01 |
| CH609035A5 (en) | 1979-02-15 |
| CH609036A5 (en) | 1979-02-15 |
| SU575021A3 (ru) | 1977-09-30 |
| PL94231B1 (enExample) | 1977-07-30 |
| CH609037A5 (en) | 1979-02-15 |
| PL95668B1 (pl) | 1977-11-30 |
| SU521838A3 (ru) | 1976-07-15 |
| DE2405322A1 (de) | 1975-09-04 |
| SU528866A3 (ru) | 1976-09-15 |
| CH609329A5 (en) | 1979-02-28 |
| CH592609A5 (enExample) | 1977-10-31 |
| SU527134A3 (ru) | 1976-08-30 |
| PL96532B1 (pl) | 1977-12-31 |
| PL94232B1 (enExample) | 1977-07-30 |
| PL96785B1 (pl) | 1978-01-31 |
| PL94279B1 (enExample) | 1977-07-30 |
| PL94234B1 (enExample) | 1977-07-30 |
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