Imidazole → 1H-Imidazole-1-propanamine

Participants

Reaction Steps

Following the procedure of Schwan, J. Het. Chem. 4, 633 (1967), 25 ml. of acrylonitrile was heated to 70° C. A 13.6 g. portion of imidazole was added and the mixture was gradually heated to 90°-100° C. and maintained at that temperature for 3 hours. The mixture was then concentrated in vacuo to remove excess acrylonitrile, taken up in methanol and reconcentrated. The concentrate was added to 150 ml. of methanol, 100 ml. of concentrated ammonium hydroxide and 8 g. of Raney nickel catalyst in a Parr apparatus and subjected to hydrogenation at an initial pressure of 53 psi. After approximately 6 hours and the uptake of 32 psi. of hydrogen, the mixture was filtered. The filtrate was concentrated to remove the solvent, then concentrated once from ethanol, giving 1H-imidazole-1-propanamine as an oil. When this was added to 250 ml. of methanolic hydrogen chloride, concentrated to remove the solvent, boiled with 100 ml. of ethanol and then refrigerated, 20.3 g. of 1H-imidazole-1-propanamine dihydrochloride was obtained as a tan solid, m.p. 146°-150° C.

Provenance & Evidence