Ammonia → 4-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

Reaction equation

[N:1]1([CH2:10][CH2:11][C:12](=O)[CH3:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH3:15]>[Ni].C(OCC)(=O)C>[NH2:15][CH:12]([CH3:13])[CH2:11][CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Procedure

Benzimidazole (VIII) (1 mole), condensed with methylvinylketone in slight excess (1-1.1 mole), in the presence of a catalytic amount of Triton B (benzyltrimethylammonium hydroxide), gives 1-[1-benzimidazolyl]-3-oxo butane (IX). This reaction is conducted in a non-polar neutral solvent, such as an aromatic hydrocarbon (for example toluene) or, preferably, ethyl acetate. The ketone (IX) is converted, by known process, into its oxime ((X). The latter, by catalytic hydrogenation, in an alcoholic medium, in the presence of ammonia and Raney nickel, under pressure (20-80 bars) and heat (50° to 100° C.), results in the amine (III). ##STR6##