1-Bromo-2-Chloroethane → 1-(4-Chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochloride

HRID 3832

Reaction equation

HRID 3832 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][Cl:18]>O1CCCC1>[ClH:1].[ClH:18].[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:16][CH2:17][Cl:18])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 1348264-Chlorobenzylpiperazine

Product 1

HCID 123621271-(4-Chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochlorideYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.0 g of 1-(4-chlorobenzyl)piperazine, 14.4 g of 1-bromo-2-chloroethane and 150 ml of tetrahydrofuran was refluxed for 8 hours. The solvent was removed in vacuo, and 2N sodium hydroxide was added to the residue. The product was extracted with methylene chloride, and the extract was dried (sodium sulfate) and concentrated. The salt was precipitated with ethereal hydrochloric acid to give 13.8 g (56% of theory) of 1-(4-chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochloride as a white crystalline solid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe solvent was removed in vacuo, and 2N sodium hydroxide
  3. additionwas added to the residue
  4. extractionThe product was extracted with methylene chloride
  5. dry with materialthe extract was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe salt was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-b5880115943c4665b571bee98c011ee9
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Linked notes

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