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

HRID 280302Notes

Reaction equation

HRID 280302 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[CH2:3][NH2:4].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=O)[CH3:24])=[CH:18][CH:17]=1.C(O)(=O)/C=C/C(O)=O>C1C=CC=CC=1.CO>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[CH3:24])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 1374281-(4-Methylphenyl)propan-2-oneHCID 444972Fumaric Acid

Product 1

HCID 23322162N-[2-(4-Methylphenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (2.05 g) and 4-methylphenylacetone (1.48 g) was refluxed in benzene (70 ml) under Dean & Stark conditions for 4h. The solvent was removed under reduced pressure, replaced with methanol and sodium borohydride (3 g) added portionwise. The solvent was evaporated under reduced pressure, the residue partitioned between water and ether and the ether layer dried (MgSO4). Removal of the solvent under reduced pressure gave an oil which was dissolved in methanol and treated with an equivalent amount of methanolic fumaric acid. Evaporation of the solvent gave the title compound (fumarate salt) as a 58:42 mixture of diastereoisomers, mp 138°-144° (EtOAc).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionadded portionwise
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and ether
  5. dry with materialthe ether layer dried (MgSO4)
  6. customRemoval of the solvent under reduced pressure
  7. customgave an oil which
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4c6f8a1d954a40b789e18c44eef216a6
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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