Potassium Hydroxide → 1,1'-(Dithiodi-2,1-ethanediyl)bis[4-(4-methylbenzyl)piperazine]

Participants

Reaction Steps

A solution of bis(2-chloroethyl)disulfide (2.9 g) in dimethylsulfoxide (5 ml) is added dropwise to a warmed mixture of (4-methylbenzyl)piperazine (5.7 g), potassium hydroxide (5.0 g), and dimethylsulfoxide (55 ml). The resulting mixture is stirred an additional 4 hours after which it is poured over ice/water and the product extracted with methylene chloride, dried and concentrated. The resulting oil (6.5 g) is purified on a silica gel column (methylene chloride:methanol, 95:5), and the salt precipitated with ethereal hydrochloric acid to provide, after recrystallization from ethanol/water, 1,1'-(dithiodi-2,1-ethanediyl)bis[4-(4-methylbenzyl)piperazine] tetrahydrochloride as a white crystalline solid, m.p. 280°-282° C.

Provenance & Evidence