Hydrazine → Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-

HRID 989483Notes

Reaction equation

HRID 989483 reaction equation
[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>C1(C)C=CC=CC=1>[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 10935191cis-2-(2-Phenylcyclopentyl)isoindoline-1,3-dione

Product 1

HCID 10931745Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-Yield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Scheme IB, step C: A 1000 mL three necked flask equipped with a mechanical stirrer, thermometer, addition funnel and a reflux condenser is charged with (+,−) cis-2-(2-phenyl-cyclopentyl)-isoindole-1,3-dione (27.34 g, 93.91 mmol) and toluene (400.0 mL). To this solution was added anhydrous hydrazine (29.48 mL, 939.09 mmol) dropwise over a period of 15 minutes. Stirred reaction at room temperature for 60 minutes then heated it at 90° C.-95° C. for 6.0 hours. Cooled reaction to room temperature, filtered precipitates, washed cake with toluene (50.0 mL) and concentrated filtrate to provide the title compound as an oil (mass=15.13 g);

Workup

  1. additionthermometer, addition funnel and a reflux condenser
  2. customreaction at room temperature for 60 minutes
  3. temperaturethen heated it at 90° C.-95° C. for 6.0 hours
  4. temperatureCooled
  5. customreaction to room temperature
  6. filtrationfiltered
  7. customprecipitates
  8. washwashed cake with toluene (50.0 mL) and concentrated filtrate

Sources & evidence

ORD record
ord-e13aa5d1dfd14f6bba8501ea4cd2b4f0
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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