4-(Benzo(b)thienyl)acetic acid → HCID 18607187, compound

Participants

Reaction Steps

A stirred solution of benzo[b]thiophene-4-acetic acid (0.50 g, 2.6 mmol) and carbonyl di-imidazole (0.46 g, 2.8 mmol) in tetrahydrofuran (5 ml) was heated with a solution of trans-(±)-N-methyl-2-(1-piperidinyl)cyclohexanamine (0.46 g, 2.3 mmol) in tetrahydrofuran (2 ml). This mixture was heated to reflux for five minutes, concentrated in vacuo, poured into saturated aqueous sodium bicarbonate (30 ml) and extracted with dichloromethane (2×20 ml) to give an oil which on trituration with diethyl ether gave trans-(±)-N-methyl-N-[2-(1-piperidinyl)cyclohexyl]benzo[b]thiophene-4-acetamide as a crystalline solid (610 mg, 72%); VmaxC=0 (liquid film) 1635 cm-1.

Provenance & Evidence