Piperazine → 1-(Methylsulfonyl)piperazine

HRID 1090909Notes

Reaction equation

HRID 1090909 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
  2. washThe filtrate was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated down

Sources & evidence

ORD record
ord-b5d3cf06af0b4add8f6ec04f43703c98
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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