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