Imidazole → 1H-Imidazole-1-propanamine

Participants

Reaction Steps

A mixture of 41 g. of imidazole and 75 ml. of acrylonitrile was heated on a steam bath for 3 hours, then concentrated under reduced pressure to remove excess acrylonitrile. A 300 ml. portion of methanol was added to the residue together with 100 ml. of concentrated ammonium hydroxide and 8 g. of Raney nickel catalyst. This mixture was hydrogenated in a Parr apparatus until hydrogen uptake ceased and then filtered giving a light green liquid. A 300 ml. portion of tetrahydrofuran was added to this liquid and the mixture filtered through diatomaceous earth. The filtrate was concentrated twice from toluene, giving 75.2 g. of the desired intermediate as a clear oil.

Provenance & Evidence