p-Anisoyl chloride → Aniracetam

HRID 1164301Notes

Reaction equation

HRID 1164301 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.C[Si](C)(C)[N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19]>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Product 1

HCID 2196Aniracetam

Procedure

24.4 g. of p-methoxybenzoyl chloride and 22.5 g. of 1-trimethylsilyl-2-pyrrolidinone are mixed and the mixture is stirred at room temperature for 10 minutes. Then, the resulting trimethylchlorosilane is distilled off under reduced pressure in an oil bath at 80° C. The residue is triturated with 100 ml. of diethyl ether. The mixture is filtered and the filter cake is recrystallized from ethanol. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120°-121° C.

Workup

  1. distillationThen, the resulting trimethylchlorosilane is distilled off under reduced pressure in an oil bath at 80° C
  2. customThe residue is triturated with 100 ml
  3. filtrationThe mixture is filtered
  4. customthe filter cake is recrystallized from ethanol

Sources & evidence

ORD record
ord-958a4d6a889c4e44a8d0390fb30f88b0
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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