Iodoethane → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1-ethyltetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.9 g) was dissolved in acetonitrile (190 ml). To the solution were added potassium carbonate (1.65 g) and ethyl iodide (0.76 ml), and the mixture was stirred at 50° C. for 16 hours. The solvent was concentrated to 1/3 under reduced pressure, which was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/1→1/2) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1-ethyltetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.05 g) and methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2-ethyltetetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.42 g).

Provenance & Evidence