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

HRID 2309029Notes

Reaction equation

HRID 2309029 reaction equation
Cl[CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7]Cl.[CH3:9][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:12][CH:11]=1.[OH-].[K+]>CS(C)=O>[CH2:2]([N:18]1[CH2:19][CH2:20][N:15]([CH2:14][C:13]2[CH:21]=[CH:22][C:10]([CH3:9])=[CH:11][CH:12]=2)[CH2:16][CH2:17]1)[CH2:3][S:4][S:5][CH2:6][CH2:7][N:18]1[CH2:19][CH2:20][N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([CH3:9])=[CH:22][CH:21]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 94964Disulfide, bis(2-chloroethyl)HCID 7647231-(4-Methylbenzyl)piperazine

Product 1

HCID 139148661,1'-(Dithiodi-2,1-ethanediyl)bis[4-(4-methylbenzyl)piperazine]

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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.

Workup

  1. extractionthe product extracted with methylene chloride
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting oil (6.5 g) is purified on a silica gel column (methylene chloride:methanol, 95:5)
  5. customthe salt precipitated with ethereal hydrochloric acid
  6. customto provide
  7. customafter 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.

Sources & evidence

ORD record
ord-eefc37b780404205bef715aaf36aab37
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

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