(Phenylmethyl)hydrazine → (+/-)-3-Benzyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione

HRID 36868

Reaction equation

HRID 36868 reaction equation
[CH:1]12[C:7](=[O:8])O[C:4](=[O:5])[CH:2]1[CH2:3]2.[CH2:9]([NH:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[CH2:9]([N:16]1[NH:17][C:7](=[O:8])[CH:1]2[CH:2]([CH2:3]2)[C:4]1=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Product 1

HCID 10680232(+/-)-3-Benzyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dioneYield 29.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 150 ml of acetonitrile was dissolved 42 g (374 mmol) of 1,2-cyclopropanedicarboxylic acid anhydride, and to the solution was added dropwise a solution of 45.8 g (374 mmol) of benzylhydrazine in 50 ml of acetonitrile, and the mixture was heated under reflux for 15 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography. Crystallization from ethyl acetate gave 24.1 g (29.7%) of the titled compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fa4eb2357689441a9fe836f52ad71c32
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Linked notes

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