Hydrochloric Acid → tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate

Participants

Reaction Steps

Combine (1-(t-butoxycarbonyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (3.2 g, 7.7 mmol), tetrahydrofuran/water (200 mL/200 mL). Add a 1 M aqueous solution of sodium hydroxide (8.4 mL, 8.4 mmol). Heat to reflux. After 18 hours, concentrate the reaction mixture in vacuo to form a solid. Dillute with water, adjust the pH to about 7 using a 1 M aqueous solution of hydrochloric acid, collect the solid by filtration, and dry to give (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine: Rf=0.38 (silica gel, 20/1 ethyl acetate/methanol).

Provenance & Evidence