Hydroxyamine hydrochloride → Spiro[2.5]octan-6-one oxime

HRID 1510142Notes

Reaction equation

HRID 1510142 reaction equation
C(O[C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8]N1CCC(=O)CC1C)(C)C.Cl.[NH2:21][OH:22].[CH3:23]C([O-])=O.[Na+]>C(O)C.O>[CH2:8]1[C:7]2([CH2:6][CH2:5][C:19](=[N:21][OH:22])[CH2:18][CH2:17]2)[CH2:23]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 667903851-(3-Isopropoxybenzyl)-2-methylpiperidin-4-one

Product 1

HCID 57336623Spiro[2.5]octan-6-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution containing 2.1 g (16.9 mmol) of the ketone from step 3 in 10 mL of ethanol was added 2.0 g (28.7 mmol) of hydroxylamine hydrochloride followed by 4.0 g (29 mmol) of NaOAc in 20 mL of water. The resulting mixture was refluxed for 3 h, cooled and concentrated to one-half volume and the precipitate was collected.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 h
  2. temperaturecooled
  3. concentrationconcentrated to one-half volume
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-7694932913324680962f869d4b06041d
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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