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Methanol → N-(3-(4-Carbomethoxyphenyl)-1-methylpropyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

HRID 434376
Notes
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Reaction equation

HRID 434376 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=O)[CH3:14])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[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].CO.[BH4-].[Na+]>C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][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:7][CH:6]=1)([O:3][CH3:4])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 4311764Sodium borohydrideHCID 109326404-(3-Oxobutyl)benzoic acid methyl ester

Product 1

HCID 20493837N-(3-(4-Carbomethoxyphenyl)-1-methylpropyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent

Procedure

A mixture of 4-(4-carbomethoxyphenyl) butan-2-one (3.0 g) and 2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine (3.0 g) in dry benzene (100 ml) was refluxed under Dean and Stark conditions for 2 hours. The solvent was replaced with methanol (100 ml) and sodium borohydride (2.0 g) was added portionwise with ice cooling. The mixture was stirred at ambient temperature for 2 hours, the solvent was evaporated and the residue was partitioned between water (100 ml) and chloroform (100 ml). The organic phase was dried (MgSO4) and evaporated to an oil, which was chromatographed on silica gel 60 in 3% methanol/chloroform. The title compound was obtained as a colourless oil.

Workup

  1. temperaturewas refluxed under Dean and Stark conditions for 2 hours
  2. additionwas added portionwise with ice cooling
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between water (100 ml) and chloroform (100 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated to an oil, which
  7. customwas chromatographed on silica gel 60 in 3% methanol/chloroform

Sources & evidence

ORD record
ord-c31c22f76520487db83f593564262688
Source dataset
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04396627

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes