Benzyl Alcohol → Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate

Participants

Reaction Steps

A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22%) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesized by the aforementioned procedure.

Provenance & Evidence