Piperazine → 1-(Benzenesulfonyl)piperazine

HRID 914971

Reaction equation

HRID 914971 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1COCC1>[C:1]1([S:7]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 8087121-(Benzenesulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzenesulfonyl chloride (1 g, 5.66 mmol) in THF (20 mL) were sequentially added triethylamine (1.97 mL, 14.15 mmol) and piperazine (2.92 g, 33.9 mmol). The reaction was stirred at room temperature for 1 hour before it was extracted with ethyl acetate and washed with water and brine. The ethyl acetate extracts were dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on silica gel (1:1 hexanes/ethyl acetate to 10/1 dichloromethane/methanol) to give 22 as a yellow oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe ethyl acetate extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (1:1 hexanes/ethyl acetate to 10/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-f7a4cdc1ca104faa8100eda6e6bfe630
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Linked notes

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