2-Pyrrolidone → Aniracetam

HRID 1164302Notes

Reaction equation

[Na].[NH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].ClC1C([O:15][C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=C(Cl)C(Cl)=C(Cl)C=1Cl>CN(C)C=O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([N:2]2[CH2:6][CH2:5][CH2:4][C:3]2=[O:7])=[O:15])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 55 °C

Procedure

7.0 g. of the sodium salt of 2-pyrrolidinone (prepared using sodium hydride) suspended in 120 ml. of dimethylformamide are added at -10° C. to a solution of 20.0 g. of p-methoxybenzoic acid pentachlorophenyl ester in 100 ml. of dimethylformamide. Subsequently, the mixture is stirred at room temperature for 1 hour and at 55° C. for 8 hours. The solvent is evaporated, the residue is treated with cold aqueous acetic acid solution and the mixture is extracted with ethyl acetate. The organic phase is washed with cold sodium bicarbonate solution and water, dried over sodium sulfate, filtered and evaporated. The residue is taken up in ethanol and stirred in an ice bath. The separated crystals are filtered off and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119°-120° C.

Workup

customThe solvent is evaporated
additionthe residue is treated with cold aqueous acetic acid solution
extractionthe mixture is extracted with ethyl acetate
washThe organic phase is washed with cold sodium bicarbonate solution and water
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
stirringstirred in an ice bath
filtrationThe separated crystals are filtered off

Sources & evidence

ORD record: ord-e5441c94127b4b68a4af1b2bc7c6bd0e
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04369139

Reaction notes

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