Methyl iodide → HCID 21273510, compound

Participants

Reaction Steps

A solution of 6.4 g (0.015 mol) of 2-[3-(N-benzyloxycarbonylmethylamino)propyl]-4,5-diphenylimidazole in 120 ml of dimethylformamide is treated at 15°-20° under argon with 0.018 mol of sodium hydride (0.8 g of a 55% dispersion in mineral oil) and thereupon stirred at room temperature for a further 30 minutes. A solution of 1.85 ml (0.03 mol) of methyl iodide in 10 ml of dimethylformamide is added thereto at 15°-20° within 15 minutes and the mixture is stirred at room temperature for a further 3 hours. After concentration under reduced pressure the residue is partitioned between ice-water and ethyl acetate. The organic phase, dried over sodium sulphate, is evaporated and the residual oil is chromatographed on 100 g of silica gel with ethyl acetate as the elution agent. The 2-[3-(N-benzyloxycarbonylmethylamino)propyl]-1-methyl-4,5-diphenylimidazole (6.4 g of oil) obtained is dissolved in 300 ml of methanol and hydrogenated at room temperature and normal pressure in the presence of 1 g of 5% palladium-on-active charcoal. The product, isolated in the usual manner, is chromatographed on 70 g of silica gel with methanol/concentrated ammonium hydroxide (100:1) as the elution agent. There are obtained 2.95 g (64%) of 1-methyl-2-[3-(methylamino)propyl]-4.5-diphenylimidazole as a thick oil.

Provenance & Evidence