Hydrochloric Acid → 1H-Benzimidazole-1-butanamine

Reaction equation

[N:1]1([CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Cl>[Pd].C(O)C>[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Procedure

A solution was prepared from 8.9 grams of the nitrile and 150 ml of absolute ethanol, 0.8 grams of palladium on charcoal and 8 ml of concentrated hydrochloric acid were added, and the resulting mixture was hydrogenated at room temperature and pressure for 48 hours. The reaction mixture was then filtered, the solvent was evaporated from the filtrate, and the residue was treated with aqueous 2 N sodium hydroxide solution and extracted with chloroform. The chloroform solution was dried and then distilled to give 1H-benzimidazole-1-butanamine boiling at about 180°-186° C. at 1.2 mm pressure.