4-Nitrobenzenesulfonyl chloride → HCID 694602, compound

HRID 2079586Notes

Reaction equation

HRID 2079586 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].C(N(CC)CC)C>ClCCl>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][OH:9])[CH2:2][CH2:3]2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 76771-(2-Hydroxyethyl)piperazineHCID 8471Triethylamine

Product 1

HCID 694602HCID 694602, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 415 μL (3.38 mmol) of 1-piperazineethanol in 20 mL of dichloromethane were added 500 mg (2.26 mmol) of 4-nitrobenzenesulfonyl chloride and 472 μL (3.38 mmol) of triethylamine under ice cooling, and the mixture was stirred for 30 minutes at the same temperature. The reaction mixture was diluted with dichloromethane and the organic layer was washed with water, saturated sodium bicarbonate aqueous solution and saturated saline solution and then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=30/1) to give 670 mg (94%) of the title compound.

Workup

  1. washthe organic layer was washed with water, saturated sodium bicarbonate aqueous solution and saturated saline solution
  2. dry with materialdried over with anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-1b95708bf45c42c2a08873bed10a7148
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Reaction notes

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