Potassium Iodide → 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane (12.1 g) in N,N-dimethylformamide (70 ml) were added 4-(2-methoxycarbonylethyl)phenethyl bromide (9.49 g), sodium carbonate (3.71 g) and potassium iodide (0.58 g), and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into an ice-water (200 ml), and the mixture was extracted with methylene chloride (200 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent to give 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (11.38 g) as a colorless oily liquid.

Provenance & Evidence