Thionyl Chloride → 3-Chloroquinolizidine

Participants

Reaction Steps

A solution of 14 g. (0.11 mole) of 3-hydroxyquinolizidine in 75 ml. of thionyl chloride and 50 ml. of benzene was refluxed for one hour. The solvent was completely evaporated, and the residue dissolved in chloroform. The solution was passed through an alumina column and evaporation of the chloroform gave crude 3-chloroquinolizidine. The crude material was chromatographed on an alumina column eluting with ether-petroleum ether, 1:19 to yield pure 3-chloroquinolizidine.

Provenance & Evidence