4-Chlorobenzaldehyde → N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

HRID 322589

반응식

HRID 322589 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.ClC1C=CC(C=O)=CC=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C:29](=O)[CH3:30])[CH:26]=[CH:27][CH:28]=1.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH:11][CH:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=2)[CH3:30])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 77264-ChlorobenzaldehydeHCID 114603-MethoxyacetophenoneHCID 5003444Sodium cyanoborohydrideHCID 64857723-(4-Chlorophenyl)propan-1-amine

생성물 1

HCID 22011071N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

시약·촉매·용매 1

HCID 11026Titanium isopropoxide촉매

실험 절차

An equal molar amount of 3-(4-chlorophenyl)propylamine (prepared in a similar fashion from 4-chlorobenzaldehyde as above) 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 I M, 5 mmol). Work-up and chromatography afforded N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 6V, as an oil; m/z (rel. int.) 303 (M+, 8), 288 (91), 196 (4), 164 (10), 135 (100), 125 (61), 103 (21), 91 (21), 77 (18).

후처리

  1. additionwere mixed 4 hr at rt

출처 및 근거

ORD 기록
ord-0d08c1404a424c6fac313457eee92acd
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211244B1

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