Potassium Carbonate → N-(4-Fluorophenyl)-N-[1-(pyridin-3-yl)ethyl]methanesulfonamide

Participants

Reaction Steps

A 10.8 g. portion of 3-[1-(4-fluorophenylamino)ethyl]pyridine was dissolved in 50 ml. of dichloromethane and 10.4 g. of potassium carbonate was added, followed by 5.9 ml. of methanesulfonyl chloride. The mixture was stirred for two days at ambient temperature, 1.8 ml. more methanesulfonyl chloride was added, and the mixture was then stirred under gentle reflux for four days. It was then cooled, extracted twice with water, dried and concentrated to an oil. The oil was dissolved in dichloromethane and chromatographed on silica gel, eluting with dichloromethane, then with chloroform, and finally with chloroform:acetone to obtain 10.7 g. of oily product. It crystallized upon seeding, m.p. 82°-85°.

Provenance & Evidence