Allyl bromide → HCID 13911095, compound

Participants

Reaction Steps

A solution of trans-(±)-N-methyl-N-[2-(methylamino)-cyclohexyl]benzo[b]thiophene-4-acetamide monohydrochloride (400 mg, 1.13 mmol) in dichloromethane (10 ml) was treated with aqueous potassium carbonate (30 ml) to liberate the parent amine. This oil was dissolved in ethanol (10 ml), dichloromethane (1 ml) and triethylamine (0.3 ml, 2.2 mmol) and treated with allyl bromide (257 mg, 2.1 mmol). This mixture was stirred in an oil bath at 50°-60° C. for six hours, concentrated in vacuo and partitioned between 10% aqueous potassium carbonate and dichloromethane. The organic fractions furnished an oil which after silica gel chromatography (100:1 ethyl acetate-triethylamine) gave trans-(±)-N-methyl-N-(2-[methyl(2-propenyl)amino]cyclohexyl)benzo[b]thiophene-4-acetamide (270 mg, 67%); δH (CDCl3) 6.0-4.3 (3H, m); Vmax (liquid film) 1637 cm-1.

Provenance & Evidence