Hydrochloric Acid → HCID 13755070, compound

Participants

Reaction Steps

To a solution of 1-benzyl-3-(4-methoxyphenyl)piperidin-3-ol (3.5 g, 11.8 mmol) in dioxane (20 mL) was added concentrated HCl (3.6 mL, 43 mmol) and the reaction mixture was stirred overnight. The solvents were evaporated under reduced pressure and the residue was diluted with sat. bicarbonate solution (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4 and evaporated under reduced pressure to give the crude product which was purified via silica gel chromatography eluting with 30% ethyl acetate in hexane to give 1-benzyl-5-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1.5 g, 4.2 mmol, 35.6% yield). LCMS (Method 107): (ES-API), m/z 280.2 (M+H) RT=2.263 min; 1H NMR (300 MHz, DMSO-d6) δ 7.42-7.32 (m, 4H), 7.29-7.19 (m, 3H), 6.91-6.82 (m, 2H), 6.16-5.97 (m, 1H), 3.73 (s, 3H), 3.65 (d, J=2.6 Hz, 3H), 3.23 (d, J=1.9 Hz, 2H), 2.55 (s, 1H), 2.24 (d, J=3.8 Hz, 2H).

Provenance & Evidence