Date of Award
Union College Only
Bachelor of Science
β-haloalkyl amines are effective sympathetic blocking agents. An attempt was made to synthesize two β –haloakyl-amines, N-methyl, N-benzyl-β-chloro-β-(p-bromophenyl and 3,5 dichloro phenyl) ethylamine hydrochloride, in hopes that the compounds would have the pharmacological properties of a rapid onset, long duration, low toxicity, and few side effects. The basic criteria that β-haloalkylamine must have in order to display blocking properties are: tertiary amine, a β-haloakylamine group capable of forming an intermediate ethylenimonium ion, and an unsaturated ring substitute attached to the amine to allow ring stabilization. The compounds being synthesized display all these characteristics. The synthesis of N-methyl, N-benzyl- β-chloro β-(p-bromo-phenyl) ethylamine hydrochloride used p-bromacetophenone as the starting material. The p-bromacetophenone was brominated with ether and aluminum chloride. The product, p-bromophenacyl bromide was reduced with sodium borohydride in methanol. The p-bromostyrene bromohydrin was refluxed with methyl benzyl amine. Unfortunately the desired product was not removed from the oily reaction mixture. In the second synthesis three methods were used in the preparation of 3, 5 dichloroacetophenone. Method one consisted of making a Grignard from methyl iodide and magnesium and then combining it with cadmium chloride and finally adding 3, 5 dichlorobenzoyl chloride to give a 13.5% yield. The second method consisted of combining methyl lithium with 3, 5 dichloro benzoic acid and then adding water. The third method consisted of chlorinating p-amino acetophenone and then removing the amine group by making a diazonium salt. The latter two methods were unsuccessful.
Shulman, Mark Stuart, "Synthesis of N-methyl-N-benzyl-beta-chloro (substituted beta-phenyl) ethylamine hychochloride" (1973). Honors Theses. 1808.