trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide → trans-3-(1H-pyrazol-1-yl)cyclopentylamine

HRID 655153Notes

Reaction equation

HRID 655153 reaction equation
[N:1]1([C@H:6]2[CH2:10][CH2:9][C@H:8]([N:11]3C(=O)C4=CC=CC=C4C3=O)[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1>CCO>[N:1]1([C@H:6]2[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

3

Reactant 1

HCID 67133690trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide

Product 1

HCID 67135041trans-3-(1H-pyrazol-1-yl)cyclopentylamineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide (R) (1.49 g, 5.30 mmol), and hydrazinemonohydorate (0.51 mL, 10.5 mmol) in EtOH (30 mL) was stirred at reflux for 3 h. After cooling, the reaction mixture was filtered followed by the removal of solvent. The crude product was purified by column chromatography (Chromatrex, CH2Cl2/EtOH=30/1) to yield trans-3-(1H-pyrazol-1-yl)cyclopentylamine (517 mg, 65%) 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. customThe crude product was purified by column chromatography (Chromatrex, CH2Cl2/EtOH=30/1)

Sources & evidence

ORD record
ord-91a62763e3454d8ba5b9e29b698c0cbf
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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