Hydrochloric Acid → HCID 10061752, compound

HRID 1667323Notes

Reaction equation

HRID 1667323 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1/[CH:10]=[CH:11]/[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]2OCC[O:20]2)[C:14](=[O:24])[CH2:13]1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1/[CH:10]=[CH:11]/[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]=[O:20])[C:14](=[O:24])[CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10448419HCID 10448419, compound

Product 1

HCID 10061752HCID 10061752, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 3 ml of 10% hydrochloric acid was added to a solution of 818 mg of 4-[(E)-2-(2,6-dimethylphenyl)vinyl]-1-(1,3-dioxolane-2-ylmethyl)piperidin-2-one in 10 ml of tetrahydrofuran, the mixture was heated under reflux for 4.5 hours. After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 685 mg of {4-[(E)-2-(2,6-dimethylphenyl)vinyl]-2-oxopiperidin-1-yl}acetaldehyde.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec9128a92aa0457b973203078a7639aa
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

Loading…