Water → Nefiracetam

HRID 2210991Notes

Reaction equation

HRID 2210991 reaction equation
[NH2-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].Cl[CH2:10][C:11]([NH:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12].O>C1(C)C=CC=CC=1>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=1[NH:13][C:11](=[O:12])[CH2:10][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24533Sodium amideHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 71157NefiracetamYield 91.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 300 ml of toluene was suspended 9.0 g of sodium amide in a nitrogen stream, and 21.3 g of 2-pyrrolidinone was slowly added thereto dropwise. After stirring the mixture at 60° to 70° C. for 2 hours, 19.7 g of 2-chloro-N-(2,6-dimethylphenyl)acetamide was added thereto, followed by allowing to react at 60° to 70° C. for 2 hours. To the reaction mixture was added 50 ml of hot water of about 70° to 85° C., and the mixture was allowed to cool with stirring. The precipitated crystals in the aqueous layer were recovered by filtration and dried under reduced pressure to obtain 22.4 g (91%) of the titled compound.

Workup

  1. additionwas slowly added
  2. customto react at 60° to 70° C. for 2 hours
  3. temperatureto cool
  4. stirringwith stirring
  5. filtrationThe precipitated crystals in the aqueous layer were recovered by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-be6b7e36995348fc99a3285cea5608e7
Source dataset
uspto-grants-1995_10
Patent number
US05461157

Reaction notes

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