Synthesis and characterisation of octahydroacidie based Imidazolium salt

Abstract

This paper describes the synthesis and characterization of chiral octahydroacridine based imidazolium salt. The reaction of cyclohexanone, dimethylamine hydrochloride and formaldehyde under reflux affords 2-Dimethylaminomethylcyclohexanone which undergoes reaction with cyclohexanone to give 2, 2’-Dicyclohexanoylmethane. Reaction of 2, 2’-dicyclohexanoylmethane with hydroxylamine hydrochloride affords the synthesis of Sym-Octahydroacridine from which 4-chlorooctahydroacridine was obtained by oxidation, hydrolysis and halogenation of the resulting secondary alcohol. The desired chiral octahydroacridine based imidazolium salt was prepared by refluxing of mesityl imidazole and 4-chlorooctahydroacridine in THF at 90 oC in a pressure tube for two week allowing the synthesis of a new unreported chiral bidentate NHC ligand precursor.

Keywords: Nucleophilic heterocyclic carbene (NHC), octahydroacridine, ligand, mesityl imidazole