p-Anisoyl chloride → Aniracetam

HRID 1164298Notes

Reaction equation

HRID 1164298 reaction equation
[Na].[NH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:2]2[CH2:6][CH2:5][CH2:4][C:3]2=[O:7])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 120252-PyrrolidoneHCID 5360545Sodium

Product 1

HCID 2196Aniracetam

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

20.2 g. of the sodium salt of 2-pyrrolidinone (prepared using sodium hydride) suspended in 270 ml. of dimethylformamide are added in four portions at -10° C. to a solution of 37.0 g. of p-methoxybenzoyl chloride in 50 ml. of dimethylformamide. Subsequently, the mixture is stirred at room temperature for 1 hour and then at 40° C. for 4 hours. The solvent is evaporated and the residue is treated with diethyl ether and with cold sodium bicarbonate solution. The insoluble crystalline constituents are filtered off, washed with water and diethyl ether and dried in vacuo over phosphorus pentoxide. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120°-121° C.

Workup

  1. waitat 40° C. for 4 hours
  2. customThe solvent is evaporated
  3. additionthe residue is treated with diethyl ether and with cold sodium bicarbonate solution
  4. filtrationThe insoluble crystalline constituents are filtered off
  5. washwashed with water and diethyl ether
  6. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-369357618de14bff8fcf33a301d59d15
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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