Potassium Carbonate → HCID 23093664, compound

HRID 1667314Notes

Reaction equation

HRID 1667314 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6](/[CH:10]=[CH:11]/[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[C:5]([CH3:25])[CH:4]=1)#[N:2].C(=O)([O-])[O-:27].[K+].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.O>[NH2:2][C:1]([C:3]1[CH:4]=[C:5]([CH3:25])[C:6](/[CH:10]=[CH:11]/[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]2)=[C:7]([CH3:9])[CH:8]=1)=[O:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 58870174HCID 58870174, compound

Product 1

HCID 23093664HCID 23093664, compoundYield 738%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of 133 mg of tert-butyl 4-[(E)-2-(4-cyano-2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate in 5 ml of acetone and 2 ml of water, 146 mg of hydrogen peroxide-urea complex and 7 mg of potassium carbonate were added, followed by stirring overnight. Then, 221 mg of hydrogen peroxide-urea complex was added and the mixture was stirred overnight, and 293 mg of hydrogen peroxide-urea complex was further added, followed by stirring for 4 days. An aqueous solution of sodium sulfate was added to the reaction mixture and extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform-methanol) to give 134 mg of tert-butyl 4-{(E)-2-[4-(aminocarbonyl)-2,6-dimethylphenyl]vinyl}piperidine-1-carboxylate.

Workup

  1. additionwere added
  2. additionThen, 221 mg of hydrogen peroxide-urea complex was added
  3. stirringthe mixture was stirred overnight
  4. addition293 mg of hydrogen peroxide-urea complex was further added
  5. stirringby stirring for 4 days
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-bfdf631f6a4947d2952a5c2d51849d55
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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