2-Naphthalenesulfonyl chloride → HCID 8321444, compound

HRID 2186119Notes

Reaction equation

HRID 2186119 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[S:25](Cl)(=[O:27])=[O:26]>C1COCC1.CN(C=O)C>[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[S:25]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 231360Piperazin-2-one

Product 1

HCID 8321444HCID 8321444, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In THF (30 ml) and DMF (30 ml) was dissolved 2-piperazinone (3.00 g), and to the solution was added triethylamine (5.02 ml). Under ice-cooling, to the mixture was added dropwise a solution of naphthalene-2-sulfonyl chloride (8.16 g) in THF (30 ml), and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The residue was washed with sodium hydrogen carbonate solution, water and ethanol to give pale brown crystals of the title compound (7.15 g).

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. washThe residue was washed with sodium hydrogen carbonate solution, water and ethanol

Sources & evidence

ORD record
ord-63b977920fbd4c43a0fb35e617959c63
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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