P-Chloroacetophenone → N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

HRID 322591

반응식

HRID 322591 반응식
CC(C1C=CC(Cl)=CC=1)=O.CC1(C2C=CC(Cl)=CC=2)C=CC=C(C=CC#N)C1.[2H][2H].[CH3:31][CH:32]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[CH2:33][CH2:34][NH2:35].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([C:51](=O)[CH3:52])[CH:48]=[CH:49][CH:50]=1.C([BH3-])#N.[Na+]>[OH-].[Pd+2].[OH-].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)(=O)C>[CH3:31][CH:32]([C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[CH2:33][CH2:34][NH:35][CH:51]([C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([O:44][CH3:43])[CH:46]=1)[CH3:52]

참가 물질

10

반응물 6

HCID 7467P-ChloroacetophenoneHCID 114603-MethoxyacetophenoneHCID 24523DeuteriumHCID 5003444Sodium cyanoborohydrideHCID 128476573-(4-Chlorophenyl)butan-1-amineHCID 697094233-Methyl-3-(4-chlorophenyl)cinnamonitrile

생성물 1

HCID 22011060N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 9942167Palladium hydroxide촉매HCID 176Acetic Acid용매

실험 절차

In a similar fashion, 4-chloroacetophenone was used to prepare 3-methyl-3-(4-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(4-chlorophenyl)propylamine. An equal molar amount of the amine, 3′-methoxyacetophenone and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 5B/5C as an oil; m/z (rel. int.) 317 (M+, 12), 302 (74), 210 (2), 182 (4), 164 (12), 135 (100), 121 (25), 103 (40), 91 (19), 77 (28).

출처 및 근거

ORD 기록
ord-199db1daa182478cb2e4719b45613e1c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211244B1

연결된 노트

불러오는 중…