Hydrochloric Acid → HCID 19819765, compound

Participants

Reaction Steps

Hydrogen chloride gas was bubbled into a solution of 1-t-butyl-3-pyrrolidinol (146 g, 1.02 mol) in chloroform (1.01) until the reaction mixture became acidic. A solution of thionyl chloride (1.55 g, 1.3 mol) was added dropwise with warming. After the addition was completed, the reaction mixture was stirred at reflux temperature for 18 h. The chloroform and excess thionyl chloride was removed on a rotary evaporator. Cracked ice and water was added to the residue and the mixture basified with 25% sodium hydroxide solution. The mixture was extracted with chloroform, and the extract washed with brine solution. The extract was dried (Na2SO4), concentrated and distilled at 75° C./15 mm to obtain 104 g (63%) of the title compound.

Provenance & Evidence