Preparative method of synthesis of 1-(halomethyl)-(±)-3-quinuclidinol halides

Direct Synthesis of N,N-Dimethyloxazolidinium Chloride by Chloromethylation of 2-(Dimethylamino)ethanol

“…The only known method of direct synthesis of N,N-dimethyloxazolidinium chloride is based on the reaction of 2-(dimethylamino)ethanol with ethylene chlorohydrin [6]. The alkylation of tertiary amines with methylene chloride, chloroform, and diiodoethane has been studied in detail using, e.g., quinuclidinol [7] or a typical tricyclic antidepressant, imipramine [8,9], as examples. However, the alkylation of tertiary amines with dihaloalkanes, followed by cyclization to oxazolidi nium salts, has been poorly studied, and we have found no reported preparative methods for the direct synthesis of these salts from 2-(dimethylamino)ethanol.…”