Thionyl Chloride → 2-Chloromethyl-4-dimethylaminomethylpyridine hydrochloride

Participants

Reaction Steps

4-Dimethylaminomethyl-2-hydroxymethylpyridine (13.45 g) in dichloromethane (200 ml) was added dropwise to a stirred solution of thionyl chloride (30 ml) in dichloromethane (150 ml). The resulting red mixture was stirred for 1 hour then concentrated in vacuo. The residue was treated with ether (300 ml) to yield a crystalline solid. Recrystallisation from methanol/ether (1:3) yielded 2-chloromethyl-4-dimethylaminomethylpyridine hydrochloride (20.04 g) as an orange solid m.p. 202°-204°.

Provenance & Evidence