Synthesis of Dopamine Hydrochloride from Vanillin

A. Ashnagar¹*, N. Gharib Naseri² and M. Nematollahi¹

¹School of Pharmacy, Ahwaz Jundi Shapour University of Medical Sciences, Ahwaz (Iran) ²Ahwaz Faculty of Petroleum Engineering, Petroleum University of Technolog, Ahwaz (Iran)

In this research synthesis of dopamine hydrochloride was achieved in a nine step procedure from Vanillin. Acetylation of Vanillin followed by hydrolysis, resulted in the formation of Ferulic acid. Methylation of ferulic acid afforded methyl-3,4-dimethoxycinnamate which was subsequently hydrolysed to give 3,4-dimethoxycinnamic acid. Hydrogenation of the latter with amalgamated sodium resulted in the formation of 3,4-dimethoxyhydrocinnamic acid. This acid was converted to the corresponding acid chloride, then to the corresponding amide. Treatment of the amide with sodium hypochlorite resulted in the formation of 2-(3,4-dimethoxyphenyl)ethylamine. Finally, the amine was refluxed in concentrated hydrochloric acid to give dopamine hydrochloride.

Dopamine hydrochloride; 2-(3,4-dihydroxyphenyl)ethylamine hydrochloride; 3-Hydroxytyramine hydrochloride; catecholamine