1,2,3,4-Tetrahydroisoquinoline → 1-[3-[(1,2,3,4-Tetrahydroisoquinolin-1-yl)carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Participants

Reaction Steps

To a stirring solution of 1-[3-carboxybutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.800 g, 2.2 mmol) in N,N-dimethylformamide (50 ml) were added sequentially 1,2,3,4-tetrahydroisoquinoline (322 mg, 1.1 eq), 1-hydroxybenzotriazole (327 mg, 1.1 eq), and dicyclohexylcarbodiimide (500 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 concntrated 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 1.24 grams of a dark oil.

Provenance & Evidence