Triethylamine → HCID 7937715, compound

HRID 1972630Notes

Reaction equation

HRID 1972630 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 231360Piperazin-2-oneHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 7937715HCID 7937715, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-piperazinone (0.46 g, 4.59 mmol, Sigma-Aldrich, St. Louis, Mo.) and triethylamine (1.5 mL, 10.76 mmol) in CH2Cl2 (20 mL) at 0° C. was added 6-chloropyridine-3-sulfonyl chloride (0.974 g, 4.59 mmol, Organic Process Research & Development 2009, 13, 875). The resulting slurry was stirred at room temperature for 30 min and then was concentrated. The residue was mixed with saturated aqueous NaHCO3 (10 mL) and was stirred at room temperature for 1 d. The slurry was filtered, washed with water (3×5 mL), and dried under reduced pressure to give 4-((6-chloro-3-pyridinyl)sulfonyl)-2-piperazinone as a white solid (1.12 g).

Workup

  1. concentrationwas concentrated
  2. additionThe residue was mixed with saturated aqueous NaHCO3 (10 mL)
  3. stirringwas stirred at room temperature for 1 d
  4. filtrationThe slurry was filtered
  5. washwashed with water (3×5 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c403843bfc8649058de5e38a05927461
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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