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

HRID 2291690Notes

Reaction equation

HRID 2291690 reaction equation
[CH2:1]1[C:5](=[O:6])[N:4]([CH2:7][C:8]([NH2:10])=[O:9])[CH2:3][CH:2]1[OH:11].[C:12](Cl)(=[O:14])[CH3:13]>>[C:8]([CH2:7][N:4]1[CH2:3][CH:2]([O:11][C:12](=[O:14])[CH3:13])[CH2:1][C:5]1=[O:6])(=[O:9])[NH2:10]

Participants

3

Reactant 2

HCID 4626OxiracetamHCID 6367Acetyl chloride

Product 1

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

Procedure

A mixture of 5.33 g oxiracetam and 44.3 ml acetyl chloride is heated at reflux for 15 min. After cooling, the solvent is evaporated in vacuo and the oil remaining is taken up in a little aqueous sodium bicarbonate, and solid sodium bicarbonate is added with stirring until neutrality is achieved. Most of the water present is removed by treating with methyl isobutyl ketone in vacuo, the residue is taken up with methylene chloride, dried with sodium sulphate and evaporated in vacuo. The oil remaining is triturated in isopropyl alcohol/diethyl ether and recrystallised from 20:80 isopropyl alcohol/isopropyl ether to give 1-carbamoylmethyl-4-acetoxy-2-pyrrolidone which when purified by chromatography melts at 84°-86° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 min
  3. temperatureAfter cooling
  4. customthe solvent is evaporated in vacuo
  5. additionis added
  6. customMost of the water present is removed
  7. additionby treating with methyl isobutyl ketone in vacuo
  8. dry with materialdried with sodium sulphate
  9. customevaporated in vacuo
  10. customThe oil remaining is triturated in isopropyl alcohol/diethyl ether
  11. customrecrystallised from 20:80 isopropyl alcohol/isopropyl ether

Sources & evidence

ORD record
ord-d9228f717f2a48fca32d39ea3d3e0516
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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