4-Chlorobutyronitrile

With both chloro and cyano functional groups, it is a bifunctional molecule.

Cyclopropyl cyanide is prepared by reaction of 4-chlorobutyronitrile with sodium amide in liquid ammonia.

This in turn is a chief precursor to a family of compounds called pyrroloisoquinolines.

These are valuable agents in medicinal chemistry that are endowed with BAT substrate reuptake inhibitor properties, elevating the synaptic concentration of serotonin and/or catecholamines.

More recently, an alternative synthetic protocol was also reported by Maryanoff.

Synthesis: [ 1 ]
Synthesis: [ 5 ] Stereoselective: [ 6 ]