4-Piperidone → HCID 22709909, compound

HRID 352792Notes

Reaction equation

HRID 352792 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([S:26](Cl)(=[O:28])=[O:27])[S:23][C:22]=2[CH:30]=1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([S:26]([N:1]3[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]3)(=[O:28])=[O:27])[S:23][C:22]=2[CH:30]=1

Participants

5

Reactant 3

HCID 337214-PiperidoneHCID 81531DiisopropylethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chloride

Product 1

HCID 22709909HCID 22709909, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (10 ml) was suspended piperidin-4-one (monohydrochloric acid monohydrate, 1.54 g), followed by the addition of diisopropylethylamine (3.48 ml) and 6-chlorobenzo[b]thiophene-2-sulfonyl chloride (2.68 g). The resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was then added to the residue, followed by washing with 1N hydrochloric acid. After extraction, the organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (ethyl acetate methylene chloride=3:1), followed by washing with hexane, whereby the title compound (colorless prism crystals, 1.92 g) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was then added to the residue
  3. washby washing with 1N hydrochloric acid
  4. extractionAfter extraction
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column (ethyl acetate methylene chloride=3:1)
  8. washby washing with hexane, whereby the title compound (colorless prism crystals, 1.92 g)
  9. customwas obtained

Sources & evidence

ORD record
ord-ae18e98c454f4bac8f45cb539f03b758
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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