4-Chlorobenzenesulfonyl chloride → HCID 68500265, compound

HRID 15739Notes

Reaction equation

HRID 15739 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>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

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 68499919HCID 68499919, compound

Product 1

HCID 68500265HCID 68500265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94.

Workup

  1. stirringThe mixture was stirred for 24 hr
  2. custompartitioned between water (300 mL) and CH2Cl2 (300 mL)
  3. washThe organic layer was washed with 0.2 N citric acid, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue (6.7 g) was purified by flash chromatography
  8. washeluting with EtOAc-hexane (1:3) mixture

Sources & evidence

ORD record
ord-6f6f3f8b9e6743e7b8a8a979bf30dc6c
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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