Hydrochloric Acid → Ethyl 3-piperidin-4-ylbenzoate hydrochloride

Participants

Reaction Steps

To a solution of 4-(3-ethoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (10.55 g, 31.64 mmol) was added a solution of 4M HCl in dioxane (79 mL, 316.41 mmol)) at RT. After stirring overnight at RT, the solvent was evaporated under reduce pressure. The resulting yellowish viscous oil was triturated with diethylether, and filtered to give 3-piperidin-4-yl-benzoic acid ethyl ester hydrochloride salt (8.53 g, quant.). 1H-NMR (400 MHz, d6-DMSO): δ=1.81-1.86 (t, 3H), 1.91-1.98 (m, 3H), 2.50-2.52 (m, 1H (overlap with DMSO), 2.95-3.05 (m, 2H), 3.32-3.39 (m, 2H), 4.31-4.39 (q, 2H), 7.49-7.52 (m, 2H), 7.81-7.83 (m, 2H), 9.5 (br, 2H). MS: m/z=234 ((M-HCl)+1).

Provenance & Evidence