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

HRID 2290867

Reaction equation

HRID 2290867 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

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 962WaterSolvent

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-51520f7cad054d9eb13690fbfc0b08c3
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Linked notes

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