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

HRID 2309027Notes

Reaction equation

[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:17][CH2:18][S:19][S:20][CH2:21][CH2:22]Cl.[OH-].[K+]>CS(C)=O>[CH2:17]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:14]=[CH:15][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)[CH2:18][S:19][S:20][CH2:21][CH2:22][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-cyanobenzylpiperazine (4.0 g), bis(2-chloroethyl) disulfide (1.9 g), potassium hydroxide (5.0 g), and dimethylsulfoxide (50 ml) is heated at 80° C. until the solution turns pink in color. The heat is then removed and the reaction mixture allowed to stir overnight at room temperature. The solution is diluted with water, and the product extracted with ether, dried, and concentrated to give 4.4 g of an oil, which is purified on a silica gel column (methylene chloride: methanol, 98:2). The resulting light brown oil is dissolved in ether and the salt precipitated with ethereal hydrochloric acid to give, after recrystallization from aqueous ethanol, 1,1'-(dithiodi-2,1-ethanediyl)bis[4-(4-cyanobenzyl)piperazine] tetrahydrochloride as a white crystalline solid, m.p. 272°-275° C.

Workup

customThe heat is then removed
additionThe solution is diluted with water
extractionthe product extracted with ether
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-1a3335a8e3b448bfa95584de6fb15978
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04692448

Reaction notes

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