反应详情

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.

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