2-Naphthalenesulfonyl chloride → HCID 8321444, compound

HRID 1868093Notes

Reaction equation

HRID 1868093 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[S:18](Cl)(=[O:20])=[O:19].C(N(C(C)C)CC)(C)C>ClCCl>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[S:18]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one

Product 1

HCID 8321444HCID 8321444, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of piperazine-2-one (353.3 mg, 3.5 mmol) and naphthalene-2-sulfonyl chloride (800 mg, 3.5 mmol) in anhydrous dichloromethane (15 mL) was added diisopropylethylamine (1.54 mL, 8.8 mmol). The mixture was stirred for 30 min. Reaction was complete as determined by TLC. The reaction mixture was filtered, washed with hexane to give a first batch. The mother liquor washed with saturated ammonium chloride, then washed with saturated brine, separated, dried over sodium sulphate. Then hexane was added, lots of precipitate formed. The was filtered, washed with hexane to give a second batch. The two batches were combined to yield 4-(naphthalene-2-sulfonyl)-piperazin-2-one in 92.5% yield (947 mg) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 3.35-3.40 (m, 2H) 3.42-3.48 (m, 2H) 3.79 (s, 2H) 6.11 (s, 1H) 7.63-7.73 (m, 2H) 7.77 (dd, J=8.72, 1.89 Hz, 1 H) 7.94 (d, J=7.83 Hz, 1H) 7.98-8.05 (m, 2H) 8.38 (s, 1H).

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered
  3. washwashed with hexane
  4. customto give a first batch
  5. washThe mother liquor washed with saturated ammonium chloride
  6. washwashed with saturated brine
  7. customseparated
  8. dry with materialdried over sodium sulphate
  9. additionThen hexane was added
  10. customlots of precipitate formed
  11. filtrationThe was filtered
  12. washwashed with hexane
  13. customto give a second batch

Sources & evidence

ORD record
ord-88bfaf2a416646a292b0eb2ecc406043
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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