The production of tyramine via the selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst

Abstract

The selective production of primary amines is a problem that plagues heterogeneously catalysed nitrile hydrogenation reactions. Whilst the target amine tyramine (HOC₆H₄CH₂CH₂NH₂) is biochemically available through the action of enzymes, synthetic routes to this species are not widely reported. Here, a heterogeneously catalysed method is proposed that utilises a Pd/C catalyst to effect the selective hydrogenation of 4-hydroxybenzyl cyanide within a three-phase reactor. The aforementioned selectivity issues are overcome by adjustment of various experimental parameters (hydrogen supply, agitation rate, temperature, use of an auxiliary agent) that result in improved catalytic performance, such that the desired tyramine salt (tyramine hydrogen sulphate) can be produced in quantitative yield. Accordingly, through consideration of the interconnectivity of hydrogenation and hydrogenolysis processes, a selective synthetic strategy is achieved with the findings suitable for extension to other substrates of this nature.