Triethylamine → 2-[4-[3-Chloro-4-(hydroxymethyl)phenyl]-1-piperazinyl]-1-(2-benzofuranyl)-ethanone

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Reaction Steps

A solution of 2-acetylbenzofuran (3.2 g. 0.02) in ether (50 ml) was treated with bromine (3.2 g., 0.02 mole) portionwise at room temperature. The mixture rapidly decolorized to a light yellow solution that was poured into cold aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted with ether. The combined ether extracts were dried (K2CO3) and the ether was removed in vacuo, keeping the mixture cold. The gummy, off-white solid was dissolved in acetone (50 ml) and quickly added to a solution of 2-chloro-4-(1-piperazinyl)benzenemethanol (4.0 g, 0.0176 mole) and triethylamine (2.0 g, 0.902 mole) in acetone (200 ml). The mixture was stirred at room temperature for one hour, then cooled in an ice bath. The solid was collected, washed with ether, and air dried. Recrystallization from acetone-ethanol gave 3.7 g (55%), mp 169°-172°.

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