Hydrochloric Acid → 4-(4-Methoxy-2-methylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Participants

Reaction Steps

A solution of tert-butyl 4-hydroxy-4-(4-methoxy-2-methylphenyl)piperidine-1-carboxylate (2.3 g, 7.2 mmol) in 1,4-dioxane (20 mL) was chilled to 0° C. and treated with a solution of HCl in dioxane (4.0 M, 1.8 mL, 7.2 mmol). The reaction mixture was stirred at rt for 12 h, and then the solvents were evaporated to provide a crude compound which was triturated with diethyl ether to provide the desired product as a solid (1.2 g, 82%). LC/MS (Method P) RT=0.63 min. (M+H)+=204.0; 1H NMR (300 MHz, DMSO-d6) δ 9.51-9.09 (m, 2H), 7.00 (d, J=8.3 Hz, 1H), 6.79-6.71 (m, 2H), 5.52 (t, J=1.5 Hz, 1H), 3.73 (s, 3H), 3.67 (br. s., 2H), 3.26 (d, J=4.5 Hz, 2H), 2.45 (d, J=1.9 Hz, 2H), 2.25 (s, 3H)

Provenance & Evidence