Water → 4-Methanesulfonylpiperazine-1-carbaldehyde

HRID 2304240Notes

Reaction equation

HRID 2304240 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].C(N(CC)CC)C.O>ClCCl>[CH:6]([N:8]1[CH2:13][CH2:12][N:11]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 176120694-Methanesulfonylpiperazine-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.5 mL of methane sulfonylchloride in 50 mL of dichloromethane was added slowly to a solution of 4.9 g of 1-formylpiperazine and 6.1 mL of triethylamine in 100 mL of dichloromethane at 0° C. After stirring for 1 hour water was added and the organic layer was separated. The aqueous layer was extracted several times with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated to yield 5.8 g of 1-formyl-4-(methylsulfonyl)piperazine. The crude product was dissolved in 15mI of ethanol and 15 mL of aqueous 2N NaOH and stirred for 1.5 hours at 80° C. After cooling to room temperature water was added and extracted several times with dichloromethane. The combine organic layers were dried (MgSO4) and concentrated to give 2.9 g of the title compound 14b. 1H-NMR 200 MHz (DMSOd6) δ: 2.70-2.77 (4H, m), 2.83 (3H, s), 2.95-3.02 (4H, m).

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted several times with dichloromethane
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-91774a7a01ab4140b240c41d9b58e28e
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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