Recent work has focused on the syntheses of benzyl azetidines. The benzyl azetidine system is desired in order to form a tetrahydrobenzazepine system, a compound containing a seven-membered heterocyclic ring. Tetrahydrobenzazepines have biological activity and can be used in pharmaceutical and medicinal applications. A novel synthesis of benzyl azetidine has been studied using 3-bromopropylamine hydrobromide, triethylamine, and benzyl bromide, and is believed to include a series of SN2 substitution reactions and deprotonations. The variables tested to maximize the product yield of this reaction were molar equivalents of the salt and identity of the base. Thus far, it has been found that the best yield of benzyl azetidine is obtained when using 1.2 molar equivalents of the salt and triethylamine as the base. 1H-NMR, IR, and GC-MS analysis were used to characterize all intermediates and products. Synthesizing benzyl azetidines via the reduction of an imine intermediate has been previously studied in the Bradley group, but yields were low and inconsistent. A more recent literature procedure incorporates suggestions that may help to improve the initial yields obtained, and this will be further explored. Finally, conversion of the 2-bromobenzyl azetidine to the tetrahydrobenzazepine system will be attempted in the near future.

Formation and reactions of benzyl azetidine compounds

249th National Meeting (2015)

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