Dimethyl Sulfoxide → 1-(4-Methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride

HRID 3807

Reaction equation

HRID 3807 reaction equation
[CH3:1][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.[OH-].[K+].CS(C)=O.Br[CH2:22][CH2:23][CH2:24][Cl:25]>O>[ClH:25].[ClH:25].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:22][CH2:23][CH2:24][Cl:25])[CH2:9][CH2:8]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 7647231-(4-Methylbenzyl)piperazine

Product 1

HCID 201531921-(4-Methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochlorideYield 274.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.0 g of 1-(4-methylbenzyl)piperazine, 8.0 g of potassium hydroxide and 125 ml of dimethyl sulfoxide was stirred for 45 minutes. 11.8 g of 1-bromo-3-chloropropane were then added, and the mixture was stirred for an additional hour. Water was added, and the product was extracted with ether, and the extract was dried (sodium sulfate) and treated with ethereal hydrochloric acid to give 23.3 g (94% of theory) of 1-(4-methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride as a white crystalline solid.

Workup

  1. stirringthe mixture was stirred for an additional hour
  2. extractionthe product was extracted with ether
  3. dry with materialthe extract was dried (sodium sulfate)
  4. additiontreated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-077a49be5a59401b8abfc287ca092333
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Linked notes

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