1-Benzyl-3-pyrrolidinone → 3-Pyrrolidinone, 1-(phenylmethyl)-, oxime

HRID 10347

Reaction equation

HRID 10347 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:15][OH:16]>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=[N:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 698901-Benzyl-3-pyrrolidinoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 7942583-Pyrrolidinone, 1-(phenylmethyl)-, oximeYield 102.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-benzylpyrrolidin-3-one (1.0 g, 5.71 mmol) in pyridine (5 mL) is added hydroxylamine hydrochloride (0.59 g, 8.57 mmol). After stirring at 90° C. for 5 hours, the reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate, water, and brine. The organic layer is dried over MgSO4, filtered, and filtrate concentrated to afford 1-benzylpyrrolidin-3-one oxime (1.11 g) as an oil. MS CI: m/z 191 (MH+).

Workup

  1. washwashed with saturated sodium bicarbonate, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationfiltrate concentrated

Sources & evidence

ORD record
ord-03179abb6e0a461e9c57bc862974a3e0
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

Loading…