Potassium Carbonate → N-Phenyl-N-[(pyridin-3-yl)methyl]methanesulfonamide

Participants

Reaction Steps

A 3.7 g. portion of 3-(phenylaminomethyl)pyridine was dissolved in 20 ml. of dichloromethane, and to it was added 4.1 g. of potassium carbonate and 2.5 ml. of methanesulfonyl chloride. The mixture was stirred under reflux overnight, and was then diluted with 20 ml. of aqueous sodium bicarbonate and 20 ml. of dichloromethane. The organic phase was separated, washed with 20 ml. of water, dried over magnesium sulfate and evaporated under vacuum. The residue was triturated with diethyl ether and dried to give 4.9 g. of impure product. It was dissolved in 10 ml. of dichloromethane and 20 ml. of ethyl acetate and filtered. The filtrate was evaporated under vacuum, and the residue was triturated with petroleum ether, filtered and dried to obtain 4.4 g. of the desired product, m.p. 104°-105°.

Provenance & Evidence