Sodium Carbonate → HCID 86605587, compound

HRID 2245333Notes

Reaction equation

HRID 2245333 reaction equation
[CH2:1]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].CC([O-])=O.[Na+].Cl.[NH2:26][OH:27].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O.O>[CH2:1]([CH:5]1[C:10](=[N:26][OH:27])[CH2:9][CH2:8][N:7]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 686856063-Butyl-1-(2-phenylethyl)piperidin-4-one

Product 1

HCID 86605587HCID 86605587, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

3-Butyl-1-phenethyl-piperidine-4-one (300 mg), NaOAc (878 mg) and hydroxylamine hydrochloride (708 mg) were suspended in ethanol/water (1:1, 10 ml) and the mixture was heated to reflux for 5 hours. The clear solution that resulted from this treatment was cooled, diluted with water and basified with 10% aq. Na2CO3 to pH 10. The suspension was extracted with DCM and the organic layer was washed with brine, dried (MgSO4) and evaporated. The product was sufficiently pure for the next step. Yellowish glass, mixture of cis and trans diastereomers (332 mg). MS (ESI): 261.4 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. customThe clear solution that resulted from this treatment
  4. temperaturewas cooled
  5. extractionThe suspension was extracted with DCM
  6. washthe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. additionYellowish glass, mixture of cis and trans diastereomers (332 mg)

Sources & evidence

ORD record
ord-7a8a8308769043f3b76c1a790317e503
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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