2-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-ol → N-(3-(4-Methylphenyl)propyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

HRID 280306Notes

Reaction equation

HRID 280306 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]([OH:12])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=O)[CH3:24])=[CH:18][CH:17]=1.CC1C=CC(CCC(=O)C)=CC=1>>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][NH:11][CH2:10][CH:9]([OH:12])[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 1374281-(4-Methylphenyl)propan-2-oneHCID 54639084-(p-Tolyl)-2-butanone

Product 1

HCID 23322159N-(3-(4-Methylphenyl)propyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Procedure

The title compound was prepared in the manner described in Example 3, replacing 2-(3-chlorophenyl)-2-hydroxy ethanamine by 2-(3-trifluoromethylphenyl)-2-hydroxyethanamine, and 4-methylphenylacetone by 4-(4-methylphenyl)butan-2-one. The chromatographed material was recrystallised from hexane to give the title compound mp 52°-55° as a 44:56 ratio of diastereoisomers.

Workup

  1. customThe title compound was prepared in the manner
  2. customThe chromatographed material was recrystallised from hexane

Sources & evidence

ORD record
ord-cbacb4e120714d02b99b497a1b78102c
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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