Potassium Hydroxide → 1,1'-(Dithiodi-2, 1-ethanediyl)bis{4-[3-(4-chlorophenyl)propyl]piperazine} tetrahydrochloride

HRID 2309030Notes

Reaction equation

HRID 2309030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[Cl:17][CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23]Cl.[OH-].[K+]>CS(C)=O>[ClH:1].[ClH:17].[ClH:1].[ClH:1].[CH2:23]([N:14]1[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:16][CH2:15]1)[CH2:22][S:21][S:20][CH2:19][CH2:18][N:14]1[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 94964Disulfide, bis(2-chloroethyl)HCID 1628731-(3-(4-Chlorophenyl)propyl)piperazine

Product 1

HCID 867417771,1'-(Dithiodi-2, 1-ethanediyl)bis{4-[3-(4-chlorophenyl)propyl]piperazine} tetrahydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The procedure described in Example 12 is followed using 1[3-(4-chlorophenyl)propyl]-piperazine (4.8 g), bis(2-chloroethyl) disulfide (1.9 g), potassium hydroxide (5.0 g), and dimethylsulfoxide (50 ml). Workup as described in Example 12 provides an oil which is purified on a silica gel column (methylene chloride:methanol, 9:1). The resulting oil (1.5 g) is precipitated with ethereal hydrochloric acid and recrystallized from water/ethanol to give 1,1'-(dithiodi-2, 1-ethanediyl)bis{4-[3-(4-chlorophenyl)propyl]piperazine} tetrahydrochloride as a white crystalline solid, m.p. 284°-286° C.

Workup

  1. customprovides an oil which
  2. customis purified on a silica gel column (methylene chloride:methanol, 9:1)
  3. customThe resulting oil (1.5 g) is precipitated with ethereal hydrochloric acid
  4. customrecrystallized from water/ethanol

Sources & evidence

ORD record
ord-27a800c7063744e49481dabed4315484
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

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