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

HRID 851174Notes

Reaction equation

HRID 851174 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-15ec641f2f5448d4a2207fde1852455e
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

Loading…