Methane → Aniracetam

HRID 1164309Notes

Reaction equation

HRID 1164309 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])=[O:8])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([N:9]2[CH2:10][CH2:11][CH2:12][C:13]2=[O:14])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 1557234-p-Anisamidobutyric acid

Product 1

HCID 2196Aniracetam

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.0 g. of 4-(p-methoxybenzoylamino)butyric acid, 50 ml. of toluene and 9.2 ml. of thionyl chloride are heated at reflux for 2 hours and then the mixture is treated with decolorizing charcoal and evaporated. The residue is dissolved in methylene chloride and chromatographed over neutral aluminum oxide. The 1-(p-methoxybenzoyl)-2-pyrrolidinone, which is eluted with methylene chloride, is recrystallized from alcohol and has a melting point of 119°-120° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customevaporated
  3. dissolutionThe residue is dissolved in methylene chloride
  4. customchromatographed over neutral aluminum oxide
  5. washThe 1-(p-methoxybenzoyl)-2-pyrrolidinone, which is eluted with methylene chloride
  6. customis recrystallized from alcohol

Sources & evidence

ORD record
ord-594cd5b101394f6caa817b19323f7ec7
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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