Hydrochloric Acid → 3-Chloro-N,N-dimethyl-3-phenylpropan-1-amine--hydrogen chloride (1/1)

Participants

Reaction Steps

A solution containing 442 g. of N,N-dimethyl 3-phenyl-3-hydroxypropylamine in 5 l. of chloroform was saturated with dry gaseous hydrogen chloride. 400 ml. of thionyl chloride were added to the chloroform solution at a rate sufficient to maintain reflux. Reflux was continued for an additional 5 hours. Evaporation of the chloroform and other volatile constituents from the reaction mixture in vacuo yielded N,N-dimethyl 3-phenyl-3-chloropropylamine hydrochloride which was collected by filtration. The filter cake was washed twice with 1500 ml. portions of acetone. The washed crystals weighed about 500 g., and melted at 181°-183° C. with decomposition. An additional 30 g. of compound were obtained from the acetone wash by standard crystallization procedures. The structure of the above compound was verified by NMR and titration.

Provenance & Evidence