1-Benzylpiperazine → 6-(4-Benzyl-1-piperazinyl)hexylsulfonic acid

HRID 861903Notes

Reaction equation

HRID 861903 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]([O-:24])(=[O:23])=[O:22].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]([OH:24])(=[O:23])=[O:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 23667833Sodium 6-bromohexanesulfonate

Product 1

HCID 197005716-(4-Benzyl-1-piperazinyl)hexylsulfonic acidYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

1-Benzylpiperazine (3.5 g), sodium 6-bromohexylsulfonate (16.2 g) and dry dimethylformamide (150 ml) are added to a flask and the mixture is heated and stirred at 180° C. for 16 hours. Precipitated crystals are collected by filtration and recrystallized from ethanol-diethyl ether to give 6-(4-benzyl-1-piperazinyl)hexylsulfonic acid (4.36 g, 63.5%) as colorless prisms. mp. 228°-230° C.

Workup

  1. temperaturethe mixture is heated
  2. customPrecipitated crystals
  3. filtrationare collected by filtration
  4. customrecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-d319ee040a9247468392bb047861fabc
Source dataset
uspto-grants-1998_02
Patent number
US05716950

Reaction notes

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