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

HRID 851174ノート

反応式

HRID 851174 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15ec641f2f5448d4a2207fde1852455e
出典データセット
uspto-grants-1983_05
特許番号
US04382958

反応ノート

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