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

HRID 851499Notes

Reaction equation

HRID 851499 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].[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](=O)[CH3:28])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16].[BH4-].[Na+]>C1C=CC=CC=1.CO>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]([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)[CH3:28])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 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 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A solution of 2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine (3 g) and 4-(4-carbomethoxyphenyl)butan-2-one (3 g) in benzene was boiled for 21/2 hours with azeotropic removal of water and then evaporated to give an oil which was dissolved in methanol and this solution was treated with sodium borohydride (2 g) at 0° C. After 2 hours the solution was evaporated, diluted with water and extracted with dichloromethane and the product from the dried (MgSO4) organic extracts was chromatographed on silica gel eluting with 5% methanol in chloroform to yield the title compound as an oil; 1H n.m.r. τ(CDCl3) 2.00-2.90 (m, 8H); 5.33 (m,1H); 6.12 (s,3H); 6.92-7.57 (m,7H; 2H exchangeable on D2O wash); 8.16-8.50 (m,2H); 8.91 (d,3H). The product was isolated as the hydrochloride salt m.p. 147.5°-150.5° C., as a 55:45 mixture of diastereoisomers.

Workup

  1. custom2 hours
  2. customwith azeotropic removal of water
  3. customevaporated
  4. customto give an oil which
  5. customAfter 2 hours the solution was evaporated
  6. additiondiluted with water
  7. extractionextracted with dichloromethane
  8. dry with materialthe product from the dried (MgSO4) organic extracts
  9. customwas chromatographed on silica gel eluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-3edfbf36c7674220bbf33ce99710dacb
Source dataset
uspto-grants-1983_05
Patent number
US04385066

Reaction notes

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