cis-N-[3-(3-pyridyl)cyclohexyl]phthalimide → cis-3-(3-Pyridyl)cyclohexylamine

HRID 655175Notes

Reaction equation

HRID 655175 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([N:13]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[CH2:12][CH2:11][CH2:10][C@H:9]([NH2:13])[CH2:8]2)[CH:2]=1

Participants

3

Reactant 1

HCID 67133879cis-N-[3-(3-pyridyl)cyclohexyl]phthalimide

Product 1

HCID 67134050cis-3-(3-Pyridyl)cyclohexylamineYield 36,904.199%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-N-[3-(3-pyridyl)cyclohexyl]phtalimide (1.64 g, 5.35 mmol) and hydrazinemonohydorate (0.52 mL, 10.7 mmol) in EtOH (25 mL) was stirred at room temperature for 2 h. The reaction mixture was filtered followed by the removal of solvent. The crude product was purified by column chromatography (NH, EtOAc) to yield cis-3-(3-pyridyl)cyclohexylamine (348 g, 37%) as colorless 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, EtOAc)

Sources & evidence

ORD record
ord-3d83ef17f8a24d90af4e87a4c80cbbfe
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

Loading…