Hydrogen Peroxide → HCID 66816823, compound

HRID 1754899Notes

Reaction equation

HRID 1754899 reaction equation
[OH-:1].[Na+].OO.[Cl:5][C:6]1[CH:7]=[C:8]([S:12]([N:15]2[CH2:20][CH2:19][C:18]([NH:23][C:24]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=O)([C:21]#[N:22])[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1.O>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([S:12]([N:15]2[CH2:20][CH2:19][C:18]3([N:23]=[C:24]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)[NH:22][C:21]3=[O:1])[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 66816521HCID 66816521, compound

Product 1

HCID 66816823HCID 66816823, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 6 M aqueous sodium hydroxide solution (0.74 mL) and a 30% aqueous hydrogen peroxide solution (0.25 mL) were added to a solution of cyclohexanecarboxylic[1-(3-chloro-benzenesulfonyl)-4-cyano-piperidin-4-yl]-amide (100 mg, 0.244 mmol) in ethanol (1.60 mL), and the mixture was heated under reflux for 4.5 hours. The reaction mixture was cooled to room temperature and water was then added, followed by concentration under reduced pressure. The residue was neutralized with a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=90:10) to give 8-(3-chloro-benzenesulfonyl)-2-cyclohexyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a white solid (52 mg, 52%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hours
  3. concentrationfollowed by concentration under reduced pressure
  4. extractionfollowed by extraction with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=90:10)

Sources & evidence

ORD record
ord-d39cd14c701248eab70942a99d18308c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…