Hydrazine hydrate (1:1) → Nebracetam

HRID 1587293Notes

Reaction equation

HRID 1587293 reaction equation
C1(=O)[N:5]([CH2:6][CH:7]2[CH2:11][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9](=[O:19])[CH2:8]2)C(=O)C2=CC=CC=C12.O.NN.C(O)(=O)/C=C/C(O)=O>C(O)C>[CH2:12]([N:10]1[CH2:11][CH:7]([CH2:6][NH2:5])[CH2:8][C:9]1=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 444972Fumaric AcidHCID 13504016HCID 13504016, compound

Product 1

HCID 65926Nebracetam

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

54 g (0.16 mol) of 4-phthalimidomethyl-1-benzyl-pyrrolidin-2-one are stirred into 1.3 l of ethyl alcohol after the addition of 32 g of hydrazine hydrate for 4 hours at room temperature. The precipitate (phthalic acid hydrazide) is removed by suction filtering the filtrate is evaporated down. 500 ml of methylene choloride are added to the residue which is then extracted three times with 100 ml of water. The organic phase is dried and evaporated down. The residue remaining is dissolved in 500 ml of methanol and 20 g (0.17 mol) of solid fumaric acid are added in batches thereto, with stirring, at boiling temperature. As the mixture cools, colorless crystals are precipitated, which are then suction filtered and washed with methanol and ether.

Workup

  1. customThe precipitate (phthalic acid hydrazide) is removed by suction
  2. filtrationfiltering the filtrate
  3. customis evaporated down
  4. addition500 ml of methylene choloride are added to the residue which
  5. extractionis then extracted three times with 100 ml of water
  6. customThe organic phase is dried
  7. customevaporated down
  8. dissolutionThe residue remaining is dissolved in 500 ml of methanol
  9. customcolorless crystals are precipitated
  10. filtrationsuction filtered
  11. washwashed with methanol and ether

Sources & evidence

ORD record
ord-d683be7d6813484895c42e091bb756df
Source dataset
uspto-grants-1993_06
Patent number
US05217967

Reaction notes

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