Water → N-[2-(4-(3-Hydroxypropoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)-ethanamine

HRID 851174노트

반응식

HRID 851174 반응식
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=O)[CH3:14])=[CH:8][CH:7]=1.[OH:16][CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[CH2:18][NH2:19].O>C1C=CC=CC=1>[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:19][CH2:18][CH:17]([OH:16])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[CH:21]=2)[CH3:14])=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 130796391-[4-(3-Hydroxypropyloxy)phenyl]propan-2-one

생성물 1

HCID 13079626N-[2-(4-(3-Hydroxypropoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)-ethanamine수율 27.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 1-[4-(3-hydroxypropoxy)phenyl]-propan-2-one (1.8 g) and 2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (1.8 g) were mixed in dry benzene (80 ml) and boiled under reflux in a Dean and Stark apparatus until water evolution was complete. The solvent was evaporated, the residue dissolved in methanol, platinum oxide (50 mg) added and the imine reduced in the presence of hydrogen at atmospheric pressure. When hydrogen uptake ceased the catalyst was removed by filtration and the solvent evaporated. The residue was chromatographed on silica-gel in 4% methanol-dichloromethane to give the title compound (0.94 g) as a colourless oil. Crystallisation from etherhexane gave a white solid, mp 97°-103°, as a 74:26 mixture of diastereoisomers.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol
  3. additionplatinum oxide (50 mg) added
  4. customwas removed by filtration
  5. customthe solvent evaporated
  6. customThe residue was chromatographed on silica-gel in 4% methanol-dichloromethane

출처 및 근거

ORD 기록
ord-15ec641f2f5448d4a2207fde1852455e
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382958

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