Oxiracetam → 1-Pyrrolidineacetamide, 4-(acetyloxy)-2-oxo-, (+-)-

HRID 1111583Notes

Reaction equation

HRID 1111583 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]([NH2:10])=[O:9])[C:4](=[O:11])[CH2:3]1.[C:12](Cl)(=[O:14])[CH3:13]>>[C:12]([O:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]([NH2:10])=[O:9])[C:4](=[O:11])[CH2:3]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 4626OxiracetamHCID 6367Acetyl chloride

Product 1

HCID 123656081-Pyrrolidineacetamide, 4-(acetyloxy)-2-oxo-, (+-)-

Procedure

A mixture of 5.53 g 2-(4-hydroxypyrrolidin-2-on-1-yl) acetamide and 44.3 ml acetyl chloride is refluxed for 15 minutes. It is then cooled, the solvent is evaporated in vacuo and the residue oil taken up with a small quantity of aqueous sodium bicarbonate, and solid sodium bicarbonate is added under stirring until neutrality. Most of the water contained in the mixture is removed by treatment in vacuo with methylisobutylketone, the residue is taken up with methylene chloride, made anhydrous over sodium sulphate and evaporated in vacuo. The residue oil is slurried into isopropyl alcohol/ethyl ether and crystallized from isopropyl alcohol/isopropyl ether (20:80) to obtain 2-(4-acetoxypyrrolidin-2-on-1-yl) acetamide, which purified by chromatography melts at 84°-86° C.

Workup

  1. temperatureis refluxed for 15 minutes
  2. temperatureIt is then cooled
  3. customthe solvent is evaporated in vacuo
  4. additionis added
  5. customis removed by treatment in vacuo with methylisobutylketone
  6. customevaporated in vacuo
  7. customcrystallized from isopropyl alcohol/isopropyl ether (20:80)

Sources & evidence

ORD record
ord-7e151de27a9a4e1fa3999456792c9855
Source dataset
uspto-grants-1978_10
Patent number
US04118396

Reaction notes

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