Water → Nefiracetam

HRID 2210990Notes

Reaction equation

HRID 2210990 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>COC(C)(C)C>[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 89.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

In 30 ml of t-butyl methyl ether was suspended 897 mg of sodium amide in a nitrogen stream, and 2.13 g of 2-pyrrolidinone was slowly added thereto dropwise, followed by refluxing for 2 hours. After allowing to cool, 1.97 g of 2-chloro-N-(2,6-dimethylphenyl)acetamide was added thereto, followed by refluxing 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 thus formed crystals in the aqueous layer were collected by filtration and dried under reduced pressure to obtain 2.19 g (89%) of the titled compound.

Workup

  1. additionwas slowly added
  2. temperatureby refluxing for 2 hours
  3. temperatureto cool
  4. temperatureby refluxing for 2 hours
  5. temperatureto cool
  6. filtrationThe thus formed crystals in the aqueous layer were collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-989f28b750024e08b6823504830822a8
Source dataset
uspto-grants-1995_10
Patent number
US05461157

Reaction notes

Loading…