Tetrahydrofuran → 1-(6-Chlorobenzo[b]thien-3-yl)-piperazine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-3-piperazinyl-benzo[b]thiophene-1,1-dioxide (6.0 g) and tetrahydrofuran (THF) (30 mL) under a nitrogen atmosphere was added a solution of D1BAL-H (diisobutylaluminum hydride) (0.084 mol) in toluene (84 mL) dropwise with ice bath cooling. The reaction mixture was stirred at 0° C. for 2 hours then overnight at room temperature. To the yellow solution was added, with vigorous stirring, water (5 ml) at a rate to control hydrogen evolution. Then 5NNaOH (5 mL) was added with rapid stirring. The resulting precipitate was filtered off and washed with dichloromethane and ether. The filtrate was concentrated in vacuo. The residue was taken up in dichloromethane (150 mL), washed with water (75 mnl) and brine (100 ml), dried over sodium sulfate and concentrated in vacuo to yield 5.93 g of a viscous gummy material which was triturated with ether. The ether fraction was concentrated in vacuo to yield 2.75 g of residue which was chromatographed (silica gel, 50% MeOH/CH2 Cl2) to yield 1.53 g product as a clear oil.

Provenance & Evidence