2-(Aminomethyl)aniline → 2-Aminobenzimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-aminobenzylamine (500 mg, 4.1 mmol) and 2-chloro-5-methoxybenzoimidazole (210 mg, 1.2 mmol) was heated at 120° C. for 18 h. The resulting oily residue was dissolved in CH2Cl2 (30 mL) and washed with H2O (30 mL). The organic layer was separated, dried over Na2SO4, and concentrated to provide crude benzimidazole amine as a solid which was treated with CDI (1.0 g, 6.0 mmol) in anhydrous DMF (15 mL). After stirring at RT for 18 h, the reaction mixture was concentrated. The residue was purified by prep TLC to give an oil which was triturated from CH2Cl2 and hexane to yield a solid. Further purification by prep HPLC provided the title compound as white solid. MS m/z: 295 (M+H+); MALDI FTMS (DHB) m/z: 295.1184 (M+H; Calc'd for C16H15N4O2, 295.1189).

Provenance & Evidence