4-Chlorobenzenesulfonyl chloride → 9-(4-Chlorobenzene-1-sulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2354893Notes

Reaction equation

HRID 2354893 reaction equation
Cl.[CH:2]12[NH:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH2:5][C:4](=[O:11])[CH2:3]2.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CCOC(C)=O>CN(C=O)C.CO>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:10]2[CH:6]3[CH2:7][CH2:8][CH2:9][CH:2]2[CH2:3][C:4](=[O:11])[CH2:5]3)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 197915239-Azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)

Product 1

HCID 161174379-(4-Chlorobenzene-1-sulfonyl)-9-azabicyclo[3.3.1]nonan-3-oneYield 69.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

20.9 g of 9-azabicyclo[3.3.1]nonan-3-one hydrochloride was dissolved in 600 mL of DMF. 89.0 g of Cs2CO3 followed by 29 g of 4-chlorobenzenesulfonyl chloride was added and the reaction mixture was stirred overnight at rt. After an additional day of stirring, the reaction mixture was poured into 1.4 L of vigorously stirring EtOAc. The mixture was stirred for 2 h and allowed to stand at rt overnight. The mixture was filtered to remove undissolved solids and the filtrate was washed with H2O (2 L×3) and brine (2 L). The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. A granular, tan solid was produced. Trituration with methanol dissolved a tan impurity to afford 9-(4-chlorophenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one as a white crystalline solid (25.9 g, 69% yield).

Workup

  1. additionwas added
  2. stirringAfter an additional day of stirring
  3. stirringThe mixture was stirred for 2 h
  4. waitto stand at rt overnight
  5. filtrationThe mixture was filtered
  6. customto remove undissolved solids
  7. washthe filtrate was washed with H2O (2 L×3) and brine (2 L)
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. customthe solvent was removed by rotary evaporation
  11. customA granular, tan solid was produced

Sources & evidence

ORD record
ord-76c7989571664d9b819c06b6a764005b
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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