Water → cis-1-(4-Chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one

HRID 15737

Reaction equation

HRID 15737 reaction equation
[CH3:1][C@H:2]1[CH2:7][C:6](=[O:8])[CH2:5][C@@H:4]([CH3:9])[NH:3]1.C(N(CC)CC)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>C(Cl)Cl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:3]2[C@H:4]([CH3:9])[CH2:5][C:6](=[O:8])[CH2:7][C@@H:2]2[CH3:1])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 13561054cis-2,6-Dimethylpiperidin-4-one

Product 1

HCID 59342367cis-1-(4-Chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude cis-2,6-dimethylpiperidin-4-one 91 from previous experiment (1.1 g, 8.6 mmol) was dissolved in CH2Cl2 (50 mL) and triethylamine (5 mL, 35 mmol) was added. Stirred solution was treated with 4-chlorobenzenesulfonyl chloride (2.2 g, 9.5 mmol). The mixture was stirred for 24 hr then was divided between water (100 mL) and CH2Cl2 (100 mL). Organic layer was washed with 0.2 N citric acid, water, brine and dried over anhydrous Na2SO4. The solution was filtered and evaporated. The residue was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture. Yield 60 mg (2% after two steps).

Workup

  1. washOrganic layer was washed with 0.2 N citric acid, water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationThe solution was filtered
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with EtOAc-hexane (1:3) mixture

Sources & evidence

ORD record
ord-71b99c62f1f846faa023e22183d00378
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Linked notes

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