trans-N-[3-(2-pyridyl)cyclopentyl]phthalimide → trans-3-(2-Pyridyl)cyclopentylamine

HRID 655140Notes

Reaction equation

HRID 655140 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9]([N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:8]1>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8]1

Participants

3

Reactant 1

HCID 59486139trans-N-[3-(2-pyridyl)cyclopentyl]phthalimide

Product 1

HCID 59486146trans-3-(2-Pyridyl)cyclopentylamineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1S,3S)-N-[3-(2-pyridyl)cyclopentyl]phthalimide (4.12 g, 14.1 mmol), and hydrazinemonohydorate (2.0 mL, 41.2 mmol) in EtOH (100 mL) was stirred at reflux for 3 h. After cooling, the reaction mixture was filtered followed by the removal of solvent. The residue was suspended in EtOAc and stirred at reflux for 1 h. After cooling, the precipitate was filtered followed by the removal of solvent to yield (1S,3S)-3-(2-pyridyl)cyclopentylamine (2.10 g, 92%) as yellow oil.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customfollowed by the removal of solvent
  5. stirringstirred
  6. temperatureat reflux for 1 h
  7. temperatureAfter cooling
  8. filtrationthe precipitate was filtered
  9. customfollowed by the removal of solvent

Sources & evidence

ORD record
ord-639706d2eda34aa3b51b7f23f33c5701
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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