[N:1]1([CH2:10][CH2:11][C:12]#[N:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[H][H].[Cl-].[Na+]>[Ni].C(O)C.O>[N:1]1([CH2:10][CH2:11][CH2:12][NH2:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1
4.2 Grams of 1H-benzimidazole-1-propionitrile, 0.2 grams sodium hydroxide, 1 gram of Raney nickel catalyst in about 100 ml of ethanol was hydrogenated at room temperature and atmospheric pressure for about 20 hours. The hydrogen uptake had stopped by this time with a total uptake of about 1300 ml. The reaction mixture was filtered and the catalyst was washed first with ethanol and then with water. The filtrates were combined and the solvent evaporated to leave a yellowish oil. The oil was dissolved in water, the water was saturated with sodium chloride, and the mixture was extracted with three portions of methylene chloride. The methylene chloride extracts were combined, washed with sodium chloride solution and then dried over potassium carbonate. The mixture was then filtered and the solvent evaporated to leave yellowish oil which was then distilled to give 1H-benzimidazole-1-propanamine boiling at 167°-170° C. at 1-1.3 mm pressure.
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