Benzoyl chloride → Triethylamine hydrochloride

Participants

Reaction Steps

N-(4-Piperidinylmethyl)benzamide was synthesized by the dropwise addition of 0.12 mole benzoyl chloride to a mixture composed of 0.12 mole 4-pyridylmethylamine and 0.122 mole triethylamine in 75 ml. dry chloroform with constant stirring over a period of 30 minutes. The contents of the reaction vessel were maintained at 10°-15° C. throughout the addition of the benzoyl chloride and for a period of thirty minutes thereafter. Triethylamine hydrochloride, which formed during the course of the reaction, was removed by filtration and the remaining filtrate evacuated in vacuo to yield the crude N-(4-pyridylmethyl)benzamide intermediate. The crude product was recrystallized from aqueous alcohol to give pure product, melting point 176.7° C., 80.5% yield.

Provenance & Evidence