Hydroxyamine hydrochloride → 1-(5-Benzyl-5-azaspiro[2.4]hept-7-yl)ethanone oxime

HRID 10345Notes

Reaction equation

HRID 10345 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]([C:15](=O)[CH3:16])[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:19][OH:20]>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:14][CH:13]([C:15](=[N:19][OH:20])[CH3:16])[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21978858HCID 21978858, compound

Product 1

HCID 723905271-(5-Benzyl-5-azaspiro[2.4]hept-7-yl)ethanone oximeYield 73.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5-benzyl-5-azaspiro[2.4]hept-7-yl)ethanone (Example A2a, 3.93 g, 17.1 mmol) and hydroxylamine hydrochloride (1.78 g, 25.7 mmol) are stirred in pyridine (10 mL) at 90° C. After 20 hours, the reaction mixture is diluted with ethyl acetate and the organic layer is washed with saturated NaHCO3, water, and brine. The organic layer is dried with MgSO4, filtered, and the filtrate concentrated to afford 1-(5-benzyl-5-azaspiro[2.4]hept-7-yl)ethanone oxime as an oil (3.07 g). MSCI: m/z 245 (MH+).

Workup

  1. washthe organic layer is washed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried with MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-eebca15bfe1a40339125a48548988faa
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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