Piperazine → 1-(Isopropylsulfonyl)piperazine

HRID 2403391Notes

Reaction equation

HRID 2403391 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:14][CH:15]([S:17](Cl)(=[O:19])=[O:18])[CH3:16]>ClCCl>[CH3:14][CH:15]([S:17]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:19])=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 824082-Propanesulfonyl chloride

Product 1

HCID 225628511-(Isopropylsulfonyl)piperazineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazine (1 g) and triethylamine (1.78 mL) in dichloromethane (20 mL) at 0° C. was added dropwise 2-propanesulfonyl chloride (1.30 mL). The reaction mixture was stirred at room temperature for 16 h and then quenched with water (20 mL) and extracted into dichloromethane (2×40 mL). The combined organic layers were washed with saturated aqueous brine solution (2×40 mL), dried (MgSO4) and concentrated to afford 1-(propane-2-sulfonyl)-piperazine as a white solid (1.87 g, 84%).

Workup

  1. customquenched with water (20 mL)
  2. extractionextracted into dichloromethane (2×40 mL)
  3. washThe combined organic layers were washed with saturated aqueous brine solution (2×40 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee11a8a83c064fc18ddd3c58a741c27b
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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