Journal
CHEMPLUSCHEM
Volume 84, Issue 10, Pages 1508-1511Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.201900526
Keywords
amines; continuous flow chemistry; deuteration; nitriles; Raney nickel
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Funding
- Ministry of National Economy, National Research Development and Innovation Office [GINOP-2.3.2-15-2016-00038]
- EU [EFOP-3.6.1-16-2016-00008]
- Ministry of Human Capacities, Hungary Grant [20391-3/2018/FEKUSTRAT]
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A simple and efficient continuous flow methodology has been developed for hydrogenation and reductive deuteration of nitriles to yield primary amines and also valuable alpha,alpha-dideutero analogues. Raney nickel proved to be a useful catalyst for the transformation of a wide range of nitriles under reasonably mild conditions with excellent deuterium incorporation (>90 %) and quantitative conversion. Among known model compounds, three new deuterated primary amines were prepared. The large-scale synthesis of deuterated tryptamine was also carried out to deliver 1.1 g product under flow conditions.
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