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

HRID 655166Notes

Reaction equation

HRID 655166 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@@H:9]([N:12]3C(=O)C4=CC=CC=C4C3=O)[CH2:8]2)[CH:2]=1>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@@H:9]([NH2:12])[CH2:8]2)[CH:2]=1

Participants

3

Reactant 1

HCID 68508356(1R,3R)-N-[3-(3-pyridyl)cyclopentyl]phthalimide

Product 1

HCID 59486114(1R,3R)-3-(3-pyridyl)cyclopentylamineYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1R,3R)-N-[3-(3-pyridyl)cyclopentyl]phthalimide (3.00 g, 10.3 mmol) and hydrazinemonohydorate (1.00 mL, 20.5 mmol) in EtOH (40 mL) was stirred at room temperature for 1 h. The reaction mixture was filtered followed by the removal of solvent. The crude product was purified by column chromatography (NH, CHCl3/MeOH=50/1) to yield (1R,3R)-3-(3-pyridyl)cyclopentylamine (1.63 g, 97%) as yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customfollowed by the removal of solvent
  3. customThe crude product was purified by column chromatography (NH, CHCl3/MeOH=50/1)

Sources & evidence

ORD record
ord-c2a432c01a3f45afa521861e52c01a1f
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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