Trifluoroacetic acid → 1-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Participants

Reaction Steps

To a solution of 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol (7 g, 23.5 mmol) in DCM (150 mL) was added trifluoroacetic acid (2.68 g, 23.5 mmol) and the reaction mixture was stirred at rt overnight. The mixture was then evaporated under reduced pressure and partitioned between 500 mL saturated aqueous sodium bicarbonate and 500 mL of ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to yield 1-benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (5.9 g, 88% yield). LCMS (method F) RT 2.84 min, 100% AP, m/z 280.4 (M+H+).

Provenance & Evidence