Gacyclidine
Gacyclidine is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine, and specifically, is a derivative of tenocyclidine.Synthesis
The condensation of 2-methylcyclohexanone with 2-thienyllithium or 2-thienylmagnesium bromide gives cyclohexanol as a diastereomeric mixture, which was treated with sodium azide in trichloroacetic acid to yield the azide. The reduction of with lithium aluminium hydride or Raney nickel in isopropanol affords the corresponding amine, preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane by means of potassium carbonate in acetonitrile to provide the target compound as a diastereomeric mixture.
