Hydroxyamine hydrochloride → HCID 86605590, compound

HRID 2245339Notes

Reaction equation

HRID 2245339 reaction equation
[CH2:1]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:22])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].Cl.[NH2:29][OH:30]>CCO.O>[CH2:1]([N:9]1[CH2:14][CH2:13][C:12](=[N:29][OH:30])[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:22])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 68687667HCID 68687667, compound

Product 1

HCID 86605590HCID 86605590, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Phenethyl-3-phenyl-piperidine-2,4-dione (781 mg), sodium acetate (1.15 g) and hydroxylamine hydrochloride (925 mg) were suspended in EtOH/water 1:1 (25 ml) and the mixture was refluxed for 4 hours. The mixture was then poured into ice/water/1N NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated to give the crude product that was purified by flash chromatography (DCM/MeOH/NH4OH 98:2:0.25) to give the compound as a white foam (489 mg). MS (ESI): 309.4 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customto give the crude product that
  7. customwas purified by flash chromatography (DCM/MeOH/NH4OH 98:2:0.25)

Sources & evidence

ORD record
ord-5ff901a57b8f423dbe0c825fb93d03c7
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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