p-Toluenesulfonic acid → 4-(4-Bromophenyl)-1-methanesulfonyl-3,6-dihydro-2H-pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-bromo-phenyl)-1-methanesulfonyl-piperidin-4-ol (60.00 g, 179.51 mmol) and p-toluenesulfonic acid (9.37 g, 53.85 mmol) in toluene (1.08 L) is stirred at 100° C. for 16 h. The reaction is cooled to 23° C. and successively washed with 2 M aq. sodium hydroxide to pH 10, and water. The phases are separated and the organic layer is dried over anhydrous sodium sulfate, filtered and the solvent is removed. Methyl tert-butyl ether (200 mL) is added and the solid is filtered and washed with methyl tert-butyl ether to obtain 35.0 g of the title compound as a pale brown solid. MS m/e (79Br/81Br) 315, 317 (M+1).

Provenance & Evidence