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

HRID 2309024Notes

Reaction equation

HRID 2309024 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.CS(C)=O.[OH-].[K+].Br[CH2:22][CH2:23][CH2:24][Cl:25]>O>[ClH:1].[ClH:25].[Cl:1][C:2]1[CH:14]=[CH:13][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:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 1348264-Chlorobenzylpiperazine

Product 1

HCID 201531894-Chlorobenzyl-4-(3-chloropropyl)piperazine dihydrochlorideYield 146.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 1-(4-chlorobenzyl)piperazine (20.0 g) is mixed with dimethyl sulfoxide (100 ml), potassium hydroxide (15.0 g) and 1-bromo-3-chloropropane (15.0 g) at room temperature for 3 hours. Water is added to the resulting solution, the reaction product is extracted with ether, dried (magnesium sulfate), and the salt is precipitated with ethereal hydrochloric acid to yield 25.1 g of 1-(4-chlorobenzyl)-4-(3-chloropropyl)piperazine dihydrochloride as a white crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-b4925db61d2e4b03a8789b505bcdf994
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

Loading…