Dichloromethane → 1-Benzyl-4-methanesulfonyl-piperazine

HRID 1893524Notes

Reaction equation

HRID 1893524 reaction equation
ClCCl.[CH2:4]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([S:18]([CH3:17])(=[O:20])=[O:19])[CH2:13][CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 759941-Benzylpiperazine

Product 1

HCID 7795071-Benzyl-4-methanesulfonyl-piperazineYield 66.4%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To dichloromethane (50 ml) was added 1-benzylpiperazine (10.0 g, 56.73 mmol), methanesulfonyl chloride (4.4 ml, 56.85 mmol) was added under ice-cooling with stirring, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was diluted with 10% aqueous sodium carbonate solution, and extracted with dichloromethane. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (9.58 g, yield 66%) as a pale-yellow solid.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 1 hr
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-233d44c1d39540e5a355b77fb04a4256
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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