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Dimethyl Sulfoxide → Benzyl-4-(3-chloropropyl)piperazine dihydrochloride

HRID 3789
Notes
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Reaction equation

HRID 3789 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[CH2:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CS(C)=O.[OH-].[K+]>O>[ClH:5].[ClH:5].[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([CH2:2][CH2:3][CH2:4][Cl:5])[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 759941-Benzylpiperazine

Product 1

HCID 13731110Benzyl-4-(3-chloropropyl)piperazine dihydrochlorideYield 163.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

31.5 g of 1-bromo-3-chloropropane were added to a mixture of 35 g of 1-benzylpiperazine, 150 ml of dimethyl sulfoxide and 25 g of potassium hydroxide. The resulting mixture was stirred at room temperature for 3 hours. Water was added to the resulting solution, the reaction product was extracted with ether, dried (magnesium sulfate), and the salt was precipitated with ethereal hydrochloric acid to give 35.6 g (55% of theory) of 1-benzyl-4-(3-chloropropyl)piperazine dihydrochloride as a white crystalline solid.

Workup

  1. extractionthe reaction product was extracted with ether
  2. dry with materialdried (magnesium sulfate)
  3. customthe salt was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-93fa51c8f7084cf4905f1b5a5619a265
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04722926

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes