Hydrochloric Acid → 4-(3-Fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

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Reaction Steps

To a stirred solution of tert-butyl 4-(3-fluoro-4-methoxyphenyl)-4-hydroxypiperidine-1-carboxylate (6.5 g, 20 mmol) in 1,4-dioxane (100 mL) at 0° C. was added 50 mL of 1M HCl (dioxane solution) and the mixture was allowed to warm to rt and stirred for 12 h. The solvent was then removed under reduced pressure. The residue was triturated with ethyl acetate to obtain 4.5 g crude 4-(3-fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride as a solid which was was isolated by filtration and used without further purification. LCMS (Method P) RT 0.57 min, m/z 208 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37-2.61 (m, 2H), 3.12-3.38 (m, 3H) 3.80-3.94 (m, 3H) 3.95-4.12 (m, 2H) 7.10-7.29 (m, 1H) 7.33-7.44 (m, 1H) 7.51 (dd, J=13.05, 2.51 Hz, 1H) 9.27-9.63 (m, 2H).

Provenance & Evidence