Water → (2R)-1,2-dibenzyl-4-methanesulfonylpiperazine

HRID 581203Notes

Reaction equation

HRID 581203 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 53338745(R)-1,2-dibenzylpiperazine

Product 1

HCID 54418760(2R)-1,2-dibenzyl-4-methanesulfonylpiperazineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (2R)-1,2-dibenzylpiperazine (2.0 g; 7.5 mmol) in dichloromethane (30 ml), methanesulfonyl chloride (0.86 g; 7.5 mmol) was added and the mixture was stirred at ambient temperature for 1 h. Potassium carbonate (1.1 g) was added and stirring was continued for another hour. Dichloromethane (20 ml) and water (10 ml) were added and the phases were separated. The organic phase was washed with water (10 ml) and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 2.2 g of (2R)-1,2-dibenzyl-4-methanesulfonylpiperazine.

Workup

  1. stirringstirring
  2. waitwas continued for another hour
  3. customthe phases were separated
  4. washThe organic phase was washed with water (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f6cc9f1f16904ae09d0fa6a21c00b68f
Source dataset
uspto-grants-1999_07
Patent number
US05919777

Reaction notes

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