Water → 4-Methanesulfonylpiperazine-1-carbaldehyde

HRID 1008492Notes

Reaction equation

HRID 1008492 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 15 ml 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-2615d5f0f9584f52a1b72838c8d33019
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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