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Dimethyl Sulfoxide → 1-(4-Chlorobenzyl)-2,5-dimethyl-4-(3-chloropropyl)piperazine

HRID 3810
Notes
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Reaction equation

HRID 3810 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([CH2:11][N:12]2[CH2:17][CH:16]([CH3:18])[NH:15][CH2:14][CH:13]2[CH3:19])=[CH:9][CH:8]=1.[OH-].[K+].CS(C)=O>O>[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([CH2:11][N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH2:2][CH2:3][CH2:4][Cl:5])[CH2:14][CH:13]2[CH3:19])=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 223135764-Chlorobenzyl-2,5-dimethylpiperazine

Product 1

HCID 201531901-(4-Chlorobenzyl)-2,5-dimethyl-4-(3-chloropropyl)piperazineYield 58%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

22.0 g g of 1-bromo-3-chloropropane were added to a mixture of 33.0 g of 4-chlorobenzyl-2,5-dimethylpiperazine, 25.0 g of potassium hydroxide and 125 ml of dimethyl sulfoxide. After stirring the solution for 3 hours at room temperature, water was added, the product was extracted with ether, and the extract was dried (magnesium sulfate) and concentrated to give 25.8 g (58% of theory) of 1-(4-chlorobenzyl)-2,5-dimethyl-4-(3-chloropropyl)piperazine as an oil, suitable for use in the next reaction.

Workup

  1. extractionthe product was extracted with ether
  2. dry with materialthe extract was dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-73dfc2a4ed354bdeacc95510bbfc783d
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