Potassium Cyanide → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

Participants

Reaction Steps

Quinuclidinone (24.2 g, 0.19 mol) and 2,4,6-triisopropylbenzene sulphonohydrazide (72 g, 0.24 mol) (250 ml) were stirred together in anhydrous methanol for 3 hours. Potassium cyanide (33.8 g, 0.51 mol) was added and the mixture heated under reflux for 5 hours. The material isolated, after evaporation of the solvent, was partitioned between water and dichloromethane. The organic phase was dried (sodium sulphate) and evaporated and the residue fractionally distilled under reduced pressure to give 3-cyano-quinuclidine (6.1 g), approximate b.p. 95°-100° at 13 N.m-2 (0.1 mmHg).

Provenance & Evidence