Acetone → Oxiracetam

HRID 2291683Notes

Reaction equation

HRID 2291683 reaction equation
[NH:1]1C2(CCCCC2)[NH:4][CH2:3][C:2]1=[O:11].[O:12]1[CH2:22][CH:13]1[CH2:14][C:15]([O:17]CC(C)C)=O.CC(C)=O>O>[CH2:14]1[C:15](=[O:17])[N:4]([CH2:3][C:2]([NH2:1])=[O:11])[CH2:22][CH:13]1[OH:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5463767Isobutyl 3,4-epoxybutyrateHCID 131250391,4-Diazaspiro[4.5]decan-2-one

Product 1

HCID 4626Oxiracetam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of 2,2-dimethyl-4-imidazolidinone ((5); R4 =R5 =CH3) (8.70 mmoles) is dissolved in 1 ml water. 1.5 g 2-methylpropyl 3,4-epoxybutanoate ((4); X=isobutyl) (9.48 mmoles) are added and the mixture is heated at 50° for 11 h with stirring by a magnetic stirrer. Heating is then continued at the boiling point for a further 11 h. The mixture is cooled, 10 ml acetone is added, stirring is performed for 30 min and the mixture is filtered. The product obtained is crystallised from methanol to give oxiractam of m.p. 167°-70° C. as a white crystalline powder.

Workup

  1. temperaturethe mixture is heated at 50° for 11 h
  2. temperatureHeating
  3. temperatureThe mixture is cooled
  4. stirringstirring
  5. waitis performed for 30 min
  6. filtrationthe mixture is filtered
  7. customThe product obtained
  8. customis crystallised from methanol

Sources & evidence

ORD record
ord-9b2ec7021b144cc1901f98e9243d9e01
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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