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

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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.

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