CA1233482A - Process for preparing 2-hydroxy-2-phenylethylamines - Google Patents
Process for preparing 2-hydroxy-2-phenylethylaminesInfo
- Publication number
- CA1233482A CA1233482A CA000437297A CA437297A CA1233482A CA 1233482 A CA1233482 A CA 1233482A CA 000437297 A CA000437297 A CA 000437297A CA 437297 A CA437297 A CA 437297A CA 1233482 A CA1233482 A CA 1233482A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- alkyl
- ethylamine
- mixture
- phenyl
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- -1 hydroxy, carboxy, amino, aminocarbonyl Chemical group 0.000 claims description 53
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 238000007792 addition Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- SYZWOOODCAMXPL-UHFFFAOYSA-N 4-[3-[(2-hydroxy-2-phenylethyl)amino]-3-methylbutyl]benzamide Chemical compound C=1C=CC=CC=1C(O)CNC(C)(C)CCC1=CC=C(C(N)=O)C=C1 SYZWOOODCAMXPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical class C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- 239000000203 mixture Substances 0.000 description 65
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 64
- 239000000047 product Substances 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 18
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 18
- 238000004809 thin layer chromatography Methods 0.000 description 18
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 229940083608 sodium hydroxide Drugs 0.000 description 13
- AWMVMTVKBNGEAK-MRVPVSSYSA-N (S)-styrene oxide Chemical compound C1O[C@H]1C1=CC=CC=C1 AWMVMTVKBNGEAK-MRVPVSSYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229960005419 nitrogen Drugs 0.000 description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 235000013350 formula milk Nutrition 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UMPFJWRYLQLSTG-UHFFFAOYSA-N 4-(3-aminobutyl)benzamide Chemical compound CC(N)CCC1=CC=C(C(N)=O)C=C1 UMPFJWRYLQLSTG-UHFFFAOYSA-N 0.000 description 4
- SQGSWPDYJPKLHU-XPKAQORNSA-N 4-[3-[[(2s)-2-hydroxy-2-phenylethyl]amino]butyl]benzamide Chemical compound C([C@@H](O)C=1C=CC=CC=1)NC(C)CCC1=CC=C(C(N)=O)C=C1 SQGSWPDYJPKLHU-XPKAQORNSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011737 fluorine Chemical group 0.000 description 4
- 229910052731 fluorine Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229960003010 sodium sulfate Drugs 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PKSROMPNLONTJT-UHFFFAOYSA-N azanium;chloroform;methanol;hydroxide Chemical compound N.O.OC.ClC(Cl)Cl PKSROMPNLONTJT-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- ISYFTHDLBGNHQW-CQSZACIVSA-N (1s)-2-(cyclohexylamino)-1-phenylethanol Chemical compound C([C@@H](O)C=1C=CC=CC=1)NC1CCCCC1 ISYFTHDLBGNHQW-CQSZACIVSA-N 0.000 description 2
- XAOCLQUZOIZSHV-UHFFFAOYSA-N 2-(benzylamino)-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CNCC1=CC=CC=C1 XAOCLQUZOIZSHV-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- LHUDRSNXNPORPA-SNVBAGLBSA-N (1s)-2-(2-hydroxyethylamino)-1-phenylethanol Chemical compound OCCNC[C@@H](O)C1=CC=CC=C1 LHUDRSNXNPORPA-SNVBAGLBSA-N 0.000 description 1
- IMTMKAFGAHACBU-GOSISDBHSA-N (2s)-n-benzyl-2-phenyl-2-trimethylsilyloxyethanamine Chemical compound C([C@@H](O[Si](C)(C)C)C=1C=CC=CC=1)NCC1=CC=CC=C1 IMTMKAFGAHACBU-GOSISDBHSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- UADKLMIUTSBMKH-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-2-[(3-fluoro-4-methoxycyclohexyl)amino]ethanol Chemical compound C1C(F)C(OC)CCC1NCC(O)C1=CC=C(F)C(F)=C1 UADKLMIUTSBMKH-UHFFFAOYSA-N 0.000 description 1
- BREORQWYSDYNDZ-UHFFFAOYSA-N 1-(3-amino-4-chlorophenyl)-2-[2-(2-propoxyphenyl)propylamino]ethanol Chemical compound CCCOC1=CC=CC=C1C(C)CNCC(O)C1=CC=C(Cl)C(N)=C1 BREORQWYSDYNDZ-UHFFFAOYSA-N 0.000 description 1
- RAKCZNLZDRUGLX-UHFFFAOYSA-N 1-(4-butan-2-ylsulfonylphenyl)-2-[(1-chloro-2-methylpropan-2-yl)amino]ethanol Chemical compound CCC(C)S(=O)(=O)C1=CC=C(C(O)CNC(C)(C)CCl)C=C1 RAKCZNLZDRUGLX-UHFFFAOYSA-N 0.000 description 1
- FGUCQWOXCWJSKZ-HKALDPMFSA-N 1-(4-chlorophenyl)-2-[[(1s)-1-phenylethyl]amino]ethanol Chemical compound N([C@@H](C)C=1C=CC=CC=1)CC(O)C1=CC=C(Cl)C=C1 FGUCQWOXCWJSKZ-HKALDPMFSA-N 0.000 description 1
- XUIQTGUNQGNJQF-UHFFFAOYSA-N 1-[3-(dimethylamino)-4-fluorophenyl]-2-[5-[3-[(2-methylpropan-2-yl)oxy]phenyl]pentylamino]ethanol Chemical compound C1=C(F)C(N(C)C)=CC(C(O)CNCCCCCC=2C=C(OC(C)(C)C)C=CC=2)=C1 XUIQTGUNQGNJQF-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- HOYPQAWATVPOKZ-UHFFFAOYSA-N 2-(2-aminopropylamino)-1-[2,5-bis(2-methylpropylamino)phenyl]ethanol Chemical compound CC(C)CNC1=CC=C(NCC(C)C)C(C(O)CNCC(C)N)=C1 HOYPQAWATVPOKZ-UHFFFAOYSA-N 0.000 description 1
- RTPJBMWUVSTBPC-UHFFFAOYSA-N 2-(2-chlorophenyl)oxirane Chemical compound ClC1=CC=CC=C1C1OC1 RTPJBMWUVSTBPC-UHFFFAOYSA-N 0.000 description 1
- HIOFHWTUAOODBJ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)oxirane Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC1 HIOFHWTUAOODBJ-UHFFFAOYSA-N 0.000 description 1
- IJUUWUSPXYGGKY-UHFFFAOYSA-N 2-(3-methoxyphenyl)oxirane Chemical compound COC1=CC=CC(C2OC2)=C1 IJUUWUSPXYGGKY-UHFFFAOYSA-N 0.000 description 1
- OJSCTBGAASJJNC-FUKCDUGKSA-N 2-(4-chlorophenyl)-n-[(1s)-1-phenylethyl]-2-trimethylsilyloxyethanamine Chemical compound N([C@@H](C)C=1C=CC=CC=1)CC(O[Si](C)(C)C)C1=CC=C(Cl)C=C1 OJSCTBGAASJJNC-FUKCDUGKSA-N 0.000 description 1
- IBWLXNDOMYKTAD-UHFFFAOYSA-N 2-(4-chlorophenyl)oxirane Chemical compound C1=CC(Cl)=CC=C1C1OC1 IBWLXNDOMYKTAD-UHFFFAOYSA-N 0.000 description 1
- OWRNRKFMWWUCND-UHFFFAOYSA-N 2-(4-ethylanilino)ethanol Chemical compound CCC1=CC=C(NCCO)C=C1 OWRNRKFMWWUCND-UHFFFAOYSA-N 0.000 description 1
- QAWJAMQTRGCJMH-UHFFFAOYSA-N 2-(4-methylphenyl)oxirane Chemical compound C1=CC(C)=CC=C1C1OC1 QAWJAMQTRGCJMH-UHFFFAOYSA-N 0.000 description 1
- YKIUTLHCSNCTDZ-UHFFFAOYSA-N 2-(4-nitrophenyl)oxirane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1OC1 YKIUTLHCSNCTDZ-UHFFFAOYSA-N 0.000 description 1
- YWXQQZANPBBUNI-UHFFFAOYSA-N 2-(benzylamino)-1-(3,4-dichlorophenyl)ethanol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(O)CNCC1=CC=CC=C1 YWXQQZANPBBUNI-UHFFFAOYSA-N 0.000 description 1
- MGFNMZOXXHQLOS-UHFFFAOYSA-N 2-(chloromethylamino)-1-(3-propoxyphenyl)ethanol Chemical compound CCCOC1=CC=CC(C(O)CNCCl)=C1 MGFNMZOXXHQLOS-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- SBUQQKAXTBKUJG-UHFFFAOYSA-N 2-(tert-butylamino)-1-(4-nitrophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=C([N+]([O-])=O)C=C1 SBUQQKAXTBKUJG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- HQABIJBBSWXURM-UHFFFAOYSA-N 2-[3-(2,6-dinitrophenyl)propylamino]-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CNCCCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O HQABIJBBSWXURM-UHFFFAOYSA-N 0.000 description 1
- VBSJCUBZUHDBEY-UHFFFAOYSA-N 2-[3-(2-amino-4-ethoxyphenyl)propylamino]-1-(3-nitrophenyl)ethanol Chemical compound NC1=CC(OCC)=CC=C1CCCNCC(O)C1=CC=CC([N+]([O-])=O)=C1 VBSJCUBZUHDBEY-UHFFFAOYSA-N 0.000 description 1
- MYWHRUIFSFANND-UHFFFAOYSA-N 2-amino-1-[3-[bis(2-methylpropyl)amino]phenyl]-1-(2-methylcyclopropyl)ethanol Chemical compound CC(C)CN(CC(C)C)C1=CC=CC(C(O)(CN)C2C(C2)C)=C1 MYWHRUIFSFANND-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 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
- IVHOGWLWMOPEFZ-UHFFFAOYSA-N 4-[1-hydroxy-2-(3-phenylbutylamino)ethyl]-1-n,3-n-dimethylbenzene-1,3-dicarboxamide Chemical compound CNC(=O)C1=CC(C(=O)NC)=CC=C1C(O)CNCCC(C)C1=CC=CC=C1 IVHOGWLWMOPEFZ-UHFFFAOYSA-N 0.000 description 1
- BZHGAYPCARNFID-UHFFFAOYSA-N 4-[1-hydroxy-2-[4-(3-methoxyphenyl)butylamino]ethyl]-3-propan-2-ylsulfonylbenzamide Chemical compound COC1=CC=CC(CCCCNCC(O)C=2C(=CC(=CC=2)C(N)=O)S(=O)(=O)C(C)C)=C1 BZHGAYPCARNFID-UHFFFAOYSA-N 0.000 description 1
- JMFWIKLONLSAGC-UHFFFAOYSA-N 5-[2-[(3-amino-2-ethylbutyl)amino]-1-hydroxyethyl]-1-n,3-n-diethylbenzene-1,3-dicarboxamide Chemical compound CCNC(=O)C1=CC(C(O)CNCC(CC)C(C)N)=CC(C(=O)NCC)=C1 JMFWIKLONLSAGC-UHFFFAOYSA-N 0.000 description 1
- DDGCKQRKWIIJFP-UHFFFAOYSA-N 5-[4-[[2-(3-ethoxyphenyl)-2-hydroxyethyl]amino]butan-2-yl]benzene-1,3-dicarbaldehyde Chemical compound CCOC1=CC=CC(C(O)CNCCC(C)C=2C=C(C=O)C=C(C=O)C=2)=C1 DDGCKQRKWIIJFP-UHFFFAOYSA-N 0.000 description 1
- AYKSADSWMYASCN-UHFFFAOYSA-N 5-carbamoyl-2-[3-[[2-hydroxy-2-[4-(propylamino)phenyl]ethyl]amino]propyl]benzoic acid Chemical compound C1=CC(NCCC)=CC=C1C(O)CNCCCC1=CC=C(C(N)=O)C=C1C(O)=O AYKSADSWMYASCN-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 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 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- COGHULFKDPMALX-UHFFFAOYSA-N P(=O)([O-])([O-])[O-].C(CCC)[NH2+]CCCC.O.CO.C(CCC)[NH2+]CCCC.C(CCC)[NH2+]CCCC Chemical compound P(=O)([O-])([O-])[O-].C(CCC)[NH2+]CCCC.O.CO.C(CCC)[NH2+]CCCC.C(CCC)[NH2+]CCCC COGHULFKDPMALX-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- XDFFYJGKULMBKM-UHFFFAOYSA-N azanium;acetonitrile;acetate;hydrate Chemical compound [NH4+].O.CC#N.CC([O-])=O XDFFYJGKULMBKM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- FIPJPVNUBMPTNM-UHFFFAOYSA-N butyl 4-[4-[[2-[3-(dimethylamino)phenyl]-2-hydroxyethyl]amino]butyl]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1CCCCNCC(O)C1=CC=CC(N(C)C)=C1 FIPJPVNUBMPTNM-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- YEXPEXVZXAVGJZ-UHFFFAOYSA-N ethyl 5-acetyl-2-[4-[[2-(3-ethoxyphenyl)-2-hydroxyethyl]amino]butyl]benzoate Chemical compound CCOC(=O)C1=CC(C(C)=O)=CC=C1CCCCNCC(O)C1=CC=CC(OCC)=C1 YEXPEXVZXAVGJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- UKJFVOWPUXSBOM-UHFFFAOYSA-N hexane;oxolane Chemical compound C1CCOC1.CCCCCC UKJFVOWPUXSBOM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- CXALKVCCFXJRKT-UHFFFAOYSA-N methanol;propan-2-ol;hydrate Chemical compound O.OC.CC(C)O CXALKVCCFXJRKT-UHFFFAOYSA-N 0.000 description 1
- HFDBIGPYNNORDB-UHFFFAOYSA-N methyl 4-[[(2-hydroxy-2-phenylethyl)amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CNCC(O)C1=CC=CC=C1 HFDBIGPYNNORDB-UHFFFAOYSA-N 0.000 description 1
- YMRUQQICJOPPPK-UHFFFAOYSA-N n,n-diethylethanamine;heptane;oxolan-2-ylmethanol Chemical compound CCCCCCC.CCN(CC)CC.OCC1CCCO1 YMRUQQICJOPPPK-UHFFFAOYSA-N 0.000 description 1
- VEEVRESMKUPSHF-UHFFFAOYSA-N n-benzyl-2-(3-methoxyphenyl)-2-trimethylsilyloxyethanamine Chemical compound COC1=CC=CC(C(CNCC=2C=CC=CC=2)O[Si](C)(C)C)=C1 VEEVRESMKUPSHF-UHFFFAOYSA-N 0.000 description 1
- ARSMQXDRZHQRTA-UHFFFAOYSA-N n-butylbutan-1-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCCNCCCC.CCCCNCCCC.CCCCNCCCC ARSMQXDRZHQRTA-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/34—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton and at least one hydroxy group bound to another carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42478582A | 1982-09-27 | 1982-09-27 | |
| US424,785 | 1982-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1233482A true CA1233482A (en) | 1988-03-01 |
Family
ID=23683863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437297A Expired CA1233482A (en) | 1982-09-27 | 1983-09-22 | Process for preparing 2-hydroxy-2-phenylethylamines |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0104888B1 (enExample) |
| JP (1) | JPS5980640A (enExample) |
| KR (1) | KR870001061B1 (enExample) |
| CA (1) | CA1233482A (enExample) |
| DE (1) | DE3366914D1 (enExample) |
| DK (1) | DK432683A (enExample) |
| GB (1) | GB2130201B (enExample) |
| GR (1) | GR78972B (enExample) |
| IL (1) | IL69788A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3306160A1 (de) * | 1983-02-22 | 1984-08-23 | Bayer Ag, 5090 Leverkusen | Wachstumsfoerdernde aminophenylethylamin-derivate |
| DE3409270A1 (de) * | 1984-03-14 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Monosilylierte aminophenylethylamin-derivate, verfahren zu ihrer herstellung und ihre verwendung zur wachstumsfoerderung |
| EP0558824A1 (en) * | 1992-02-04 | 1993-09-08 | Duphar International Research B.V | Method for the preparation of vicinal aminoalcohols and optically active O-protected derivatives thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL57671A (en) * | 1978-07-03 | 1982-11-30 | Lilly Co Eli | Phenethanolamines,process for their preparation and pharmaceutical and animal feed compositions containing the same |
-
1983
- 1983-09-21 IL IL69788A patent/IL69788A/xx unknown
- 1983-09-21 JP JP58176187A patent/JPS5980640A/ja active Pending
- 1983-09-22 EP EP83305613A patent/EP0104888B1/en not_active Expired
- 1983-09-22 DE DE8383305613T patent/DE3366914D1/de not_active Expired
- 1983-09-22 GB GB08325359A patent/GB2130201B/en not_active Expired
- 1983-09-22 DK DK432683A patent/DK432683A/da not_active Application Discontinuation
- 1983-09-22 CA CA000437297A patent/CA1233482A/en not_active Expired
- 1983-09-22 GR GR72504A patent/GR78972B/el unknown
- 1983-09-23 KR KR1019830004460A patent/KR870001061B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0104888B1 (en) | 1986-10-15 |
| IL69788A (en) | 1987-01-30 |
| KR870001061B1 (ko) | 1987-05-27 |
| GB2130201B (en) | 1986-06-04 |
| DK432683A (da) | 1984-03-28 |
| EP0104888A1 (en) | 1984-04-04 |
| DK432683D0 (da) | 1983-09-22 |
| GB8325359D0 (en) | 1983-10-26 |
| JPS5980640A (ja) | 1984-05-10 |
| IL69788A0 (en) | 1983-12-30 |
| DE3366914D1 (en) | 1986-11-20 |
| KR840006326A (ko) | 1984-11-29 |
| GB2130201A (en) | 1984-05-31 |
| GR78972B (enExample) | 1984-10-02 |
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