Piperazine → 1-((Trifluoromethyl)sulfonyl)piperazine

HRID 2403387Notes

Reaction equation

HRID 2403387 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:14][C:15]([F:21])([F:20])[S:16](Cl)(=[O:18])=[O:17]>ClCCl>[F:14][C:15]([F:21])([F:20])[S:16]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 186908331-((Trifluoromethyl)sulfonyl)piperazineYield 76%

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 trifluoromethanesulfonyl chloride (1.24 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-trifluoromethanesulfonyl-piperazine as a pale yellow solid (1.92 g, 76%).

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-e65685402b1744f192415d45e5771285
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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