SU530638A3 - Способ получени бензиламинов - Google Patents
Способ получени бензиламиновInfo
- Publication number
- SU530638A3 SU530638A3 SU1963879A SU1963879A SU530638A3 SU 530638 A3 SU530638 A3 SU 530638A3 SU 1963879 A SU1963879 A SU 1963879A SU 1963879 A SU1963879 A SU 1963879A SU 530638 A3 SU530638 A3 SU 530638A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dibromo
- melting point
- hydrochloride
- bromide
- hydroxy
- Prior art date
Links
- 150000003939 benzylamines Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 238000002844 melting Methods 0.000 description 56
- 230000008018 melting Effects 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 24
- -1 alkyl radical Chemical class 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- SPUZPJKEJXIRSF-UHFFFAOYSA-N 2,4-dibromo-6-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(Br)C=C1CBr SPUZPJKEJXIRSF-UHFFFAOYSA-N 0.000 description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- AXRZRBIBAABFEA-UHFFFAOYSA-N 2,4-dibromo-6-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=CC(Br)=C1O AXRZRBIBAABFEA-UHFFFAOYSA-N 0.000 description 5
- VAYGTMNZLZAUDL-UHFFFAOYSA-N 2,6-dibromo-4-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(CBr)C=C1Br VAYGTMNZLZAUDL-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- NIQIPYGXPZUDDP-NTSWFWBYSA-N (1r,3s)-3-aminocyclohexan-1-ol Chemical compound N[C@H]1CCC[C@@H](O)C1 NIQIPYGXPZUDDP-NTSWFWBYSA-N 0.000 description 2
- DZEJRHSZNSUZSU-UHFFFAOYSA-N 6-cyclopropylhexan-1-amine Chemical compound NCCCCCCC1CC1 DZEJRHSZNSUZSU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 2
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NIQIPYGXPZUDDP-WDSKDSINSA-N (1s,3s)-3-aminocyclohexan-1-ol Chemical compound N[C@H]1CCC[C@H](O)C1 NIQIPYGXPZUDDP-WDSKDSINSA-N 0.000 description 1
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- CCDHIPUSJOTVEL-UHFFFAOYSA-N 1-(3-bromo-5-chlorophenyl)-N-methylmethanamine Chemical compound CNCC1=CC(Cl)=CC(Br)=C1 CCDHIPUSJOTVEL-UHFFFAOYSA-N 0.000 description 1
- ZSUOUIWICDZSFL-UHFFFAOYSA-N 2,4-dibromo-6-[(2-methylbutan-2-ylamino)methyl]phenol Chemical compound CCC(C)(C)NCC1=CC(Br)=CC(Br)=C1O ZSUOUIWICDZSFL-UHFFFAOYSA-N 0.000 description 1
- ZSVIBQBJUVMLCQ-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(ethyl)amino]methyl]phenol;hydrochloride Chemical compound Cl.C1CCCCC1N(CC)CC1=CC(Br)=CC(Br)=C1O ZSVIBQBJUVMLCQ-UHFFFAOYSA-N 0.000 description 1
- JHJSXNNLXUITIR-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(propan-2-yl)amino]methyl]phenol Chemical compound C1CCCCC1N(C(C)C)CC1=CC(Br)=CC(Br)=C1O JHJSXNNLXUITIR-UHFFFAOYSA-N 0.000 description 1
- BYIPWNHIPXWBBO-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclopentyl(methyl)amino]methyl]phenol Chemical compound C1(CCCC1)N(C)CC1=C(C(=CC(=C1)Br)Br)O BYIPWNHIPXWBBO-UHFFFAOYSA-N 0.000 description 1
- GNIHGYYYCAZOCF-UHFFFAOYSA-N 2-(bromomethyl)-4,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1CBr GNIHGYYYCAZOCF-UHFFFAOYSA-N 0.000 description 1
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-UHFFFAOYSA-N 0.000 description 1
- VNNMSKDJNGPWMO-UHFFFAOYSA-N 2-bromo-6-(bromomethyl)phenol Chemical compound Oc1c(Br)cccc1CBr VNNMSKDJNGPWMO-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- GYWBAJXONZCEJD-UHFFFAOYSA-N 3-(3,5-dibromo-2-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC(Br)=CC(Br)=C1O GYWBAJXONZCEJD-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
- RVELKTSHKDTMSZ-UHFFFAOYSA-N 4-(bromomethyl)-2,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(CBr)C=C1Cl RVELKTSHKDTMSZ-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- GIWFAODVBQFQCT-UHFFFAOYSA-N 4-tert-butyl-n-propan-2-ylcyclohexan-1-amine Chemical compound CC(C)NC1CCC(C(C)(C)C)CC1 GIWFAODVBQFQCT-UHFFFAOYSA-N 0.000 description 1
- BGNLXETYTAAURD-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-amine Chemical compound CC(C)(C)C1CCC(N)CC1 BGNLXETYTAAURD-UHFFFAOYSA-N 0.000 description 1
- AFPZLJXEXNSBRL-JCNLHEQBSA-N C(C)(C)(C)[C@@H]1CC[C@H](CC1)N(CCC)CC1=C(C(=CC(=C1)Br)Br)O Chemical compound C(C)(C)(C)[C@@H]1CC[C@H](CC1)N(CCC)CC1=C(C(=CC(=C1)Br)Br)O AFPZLJXEXNSBRL-JCNLHEQBSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 206010051602 Laziness Diseases 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- HZKGZDVSYKTNSA-UHFFFAOYSA-N Oc1c(Cl)cc(CBr)cc1Br Chemical compound Oc1c(Cl)cc(CBr)cc1Br HZKGZDVSYKTNSA-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- JIJWRJCVLPNOHM-UHFFFAOYSA-N bromo(phenyl)methanol Chemical compound OC(Br)C1=CC=CC=C1 JIJWRJCVLPNOHM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229960004138 cyclobarbital Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HPTWZQNAGHDMIA-UHFFFAOYSA-N n-benzyl-2-methylbutan-2-amine Chemical compound CCC(C)(C)NCC1=CC=CC=C1 HPTWZQNAGHDMIA-UHFFFAOYSA-N 0.000 description 1
- LRXSDHDEISIWQB-UHFFFAOYSA-N n-methylcycloheptanamine Chemical compound CNC1CCCCCC1 LRXSDHDEISIWQB-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- SQGBZKZDUMBTIJ-UHFFFAOYSA-N n-prop-2-enylcyclohexanamine Chemical compound C=CCNC1CCCCC1 SQGBZKZDUMBTIJ-UHFFFAOYSA-N 0.000 description 1
- HGEXOWFANSIFAZ-UHFFFAOYSA-N n-propan-2-ylcyclopentanamine Chemical compound CC(C)NC1CCCC1 HGEXOWFANSIFAZ-UHFFFAOYSA-N 0.000 description 1
- QHZWWLYWZPCJMN-UHFFFAOYSA-N n-propylcycloheptanamine Chemical compound CCCNC1CCCCCC1 QHZWWLYWZPCJMN-UHFFFAOYSA-N 0.000 description 1
- PXKCSKRXWAZGFK-UHFFFAOYSA-N n-propylcyclohexanamine Chemical compound CCCNC1CCCCC1 PXKCSKRXWAZGFK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722251891 DE2251891C3 (de) | 1972-10-23 | Benzylamine, deren physiologisch verträglichen Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2316325A DE2316325A1 (de) | 1972-10-23 | 1973-04-02 | Neue verfahren zur herstellung von benzylaminen |
| DE19732320967 DE2320967C3 (de) | 1973-04-26 | Neue Benzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE19732337932 DE2337932A1 (de) | 1972-10-23 | 1973-07-26 | Neue verfahren zur herstellung von benzylaminen |
| DE2346743A DE2346743C3 (de) | 1972-10-23 | 1973-09-17 | 2- oder 4-Hydroxy-3,5-dihalogenbenzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU530638A3 true SU530638A3 (ru) | 1976-09-30 |
Family
ID=27510276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1963879A SU530638A3 (ru) | 1972-10-23 | 1973-10-19 | Способ получени бензиламинов |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5535374B2 (enExample) |
| AT (1) | AT330149B (enExample) |
| BE (1) | BE806375A (enExample) |
| CA (1) | CA1092113A (enExample) |
| CH (11) | CH605621A5 (enExample) |
| DD (1) | DD108974A5 (enExample) |
| DK (1) | DK149883C (enExample) |
| FI (1) | FI62051C (enExample) |
| FR (1) | FR2203639B1 (enExample) |
| GB (1) | GB1450702A (enExample) |
| HU (1) | HU168131B (enExample) |
| IE (1) | IE38961B1 (enExample) |
| NL (1) | NL180978C (enExample) |
| NO (1) | NO138251C (enExample) |
| SE (1) | SE409699B (enExample) |
| SU (1) | SU530638A3 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT332863B (de) * | 1973-01-02 | 1976-10-25 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen 2-aminomethyl-4,6-dihalogenphenolderivaten sowie deren additionssalzen mit sauren |
| DE2934508A1 (de) * | 1978-09-06 | 1980-03-20 | Sandoz Ag | Alpha -alkyl-o-oxybenzylamin- derivate, ihre herstellung und sie enthaltende heilmittel |
| US4578390A (en) * | 1981-12-14 | 1986-03-25 | Merck & Co., Inc. | Hydroxybenzylamino derivatives as anti-inflammatory agents |
| GB8606066D0 (en) * | 1986-03-12 | 1986-04-16 | Ici Plc | Bromine-containing polyols |
| DE3820292A1 (de) * | 1988-06-15 | 1990-04-12 | Basf Ag | Aminomethylphenole und diese enthaltende fungizide |
| US20100137445A1 (en) * | 2007-06-29 | 2010-06-03 | Sumitomo Chemical Company ,Limited | Plant disease control agent, and plant disease control method |
| ES2774784T3 (es) * | 2014-11-05 | 2020-07-22 | Dow Global Technologies Llc | Poliol retardante de llama |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB836934A (en) * | 1957-10-03 | 1960-06-09 | Monsanto Chemicals | Phenolic amino compounds |
-
1973
- 1973-10-16 NL NLAANVRAGE7314216,A patent/NL180978C/xx not_active IP Right Cessation
- 1973-10-19 FI FI3254/73A patent/FI62051C/fi active
- 1973-10-19 SU SU1963879A patent/SU530638A3/ru active
- 1973-10-22 NO NO4087/73A patent/NO138251C/no unknown
- 1973-10-22 DK DK571973A patent/DK149883C/da active
- 1973-10-22 BE BE136949A patent/BE806375A/xx not_active IP Right Cessation
- 1973-10-22 HU HUTO938A patent/HU168131B/hu unknown
- 1973-10-22 JP JP11886973A patent/JPS5535374B2/ja not_active Expired
- 1973-10-22 IE IE01888/73A patent/IE38961B1/xx unknown
- 1973-10-22 SE SE7314321A patent/SE409699B/sv unknown
- 1973-10-22 CA CA183,899A patent/CA1092113A/en not_active Expired
- 1973-10-23 CH CH1147977A patent/CH605621A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148277A patent/CH603550A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1494973A patent/CH597148A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148377A patent/CH602575A5/xx not_active IP Right Cessation
- 1973-10-23 DD DD174238A patent/DD108974A5/xx unknown
- 1973-10-23 CH CH1148077A patent/CH602573A5/xx not_active IP Right Cessation
- 1973-10-23 FR FR7337753A patent/FR2203639B1/fr not_active Expired
- 1973-10-23 GB GB4933973A patent/GB1450702A/en not_active Expired
- 1973-10-23 CH CH1148477A patent/CH602576A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148177A patent/CH602574A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147777A patent/CH611871A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147677A patent/CH605620A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147577A patent/CH602571A5/xx not_active IP Right Cessation
-
1975
- 1975-04-23 AT AT309675A patent/AT330149B/de not_active IP Right Cessation
-
1977
- 1977-09-20 CH CH1147877A patent/CH602572A5/xx not_active IP Right Cessation
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