Benzylamine → (RS) 1-[3-[[benzylaminoamino]carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Participants

Reaction Steps

To a stirring solution of (RS) 1-[3-carboxybutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.500 g, 1.4 mmol) in N,N-dimethylformamide (40 ml) were added sequentially benzylamine (165 mg, 1.1 eq), 1-hydroxybenzotriazole (208 mg, 1.1 eq), and dicyclohexylcarbodiimide (317 mg, 1.1 eq). The resulting mixture was then stirred under a nitrogen atmosphere at room temperature for 64 hours. The reaction mixture was then filtered and the resulting filtrate was concentrated under reduced pressure. This residue was taken into ethyl acetate (200 ml) and washed once with water (200 ml), dried over potassium carbonate. The solvents were removed in vacuo to yield 0.714 grams of the title product as a white foam.

Provenance & Evidence