(1R,3R)-N-[3-(2-pyridyl)cyclopentyl]phthalimide → (1R,3R)-3-(2-pyridyl)cyclopentylamine

HRID 655142Notes

Reaction equation

HRID 655142 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 59486137(1R,3R)-N-[3-(2-pyridyl)cyclopentyl]phthalimide

Product 1

HCID 59486130(1R,3R)-3-(2-pyridyl)cyclopentylamineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1R,3R)-N-[3-(2-pyridyl)cyclopentyl]phthalimide (4.17 g, 14.3 mmol), and hydrazinemonohydorate (2.0 mL, 41.2 mmol) in EtOH (100 mL) was stirred at reflux for 4 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 (1R,3R)-3-(2-pyridyl)cyclopentylamine (1.62 g, 70%) as yellow oil.

Workup

  1. temperatureat reflux for 4 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-0aa8e8b89f964f658e1e481555ce7255
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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