Piperazine → 1-(4-(Methylsulfonyl)phenyl)piperazine

HRID 1792489Notes

Reaction equation

HRID 1792489 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 770141-Bromo-4-(methylsulphonyl)benzene

Product 1

HCID 7359041-(4-(Methylsulfonyl)phenyl)piperazineYield 91.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.0 g 1-bromo-4-methylsulfonyl benzene, 3.3 g piperazine and 470 mg tetrabutyl ammonium iodide was stirred at 120° C. to 140° C. for 5 hours. Water was added to the mixture, then insolubles were filtered off, the filtrate was extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography, to give 2.8 g of the title compound as a white solid.

Workup

  1. filtrationinsolubles were filtered off
  2. extractionthe filtrate was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-dc435eadabab4c7aab992d48ebc7c27f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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