Piperazine → 1-(Methylsulfonyl)piperazine

HRID 488229Notes

Reaction equation

HRID 488229 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[OH-].[Na+]>ClCCl>[CH3:1][S:2]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chloride

Product 1

HCID 7091611-(Methylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methanesulfonyl chloride (1.85 ml, 24 mmol) and piperazine (2.06 g, 24 mmol) in dichloromethane (60 ml) was stirred at room temperature for 14 hours. The mixture was basified with aqueous sodium hydroxide and filtered The filtrate was washed with water, dried (magnesium sulfate) and evaporated down to give the title sulfonamide. 1HNMR(CDCl3): 1.75 (br s, 1H), 2.78 (s, 3H), 2.97 (t, 4H, J=5.1 Hz) and 3.19 (t, 4H, J=7.5 Hz). LRMS (m/e, % abundance) 165[(M+H)+, 7), 164(M+, 5), 85(100) and 56(68).

Workup

  1. filtrationfiltered The filtrate
  2. washwas washed with water
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated down

Sources & evidence

ORD record
ord-b175ec79eaed4fbb8f7b0b6ec6949282
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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