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

HRID 655171Notes

Reaction equation

HRID 655171 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 67133459trans-N-[3-(3-pyridyl)cyclohexyl]phthalimide

Product 1

HCID 67133702trans-3-(3-Pyridyl)cyclohexylamineYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of trans-N-[3-(3-pyridyl)cyclohexyl]phthalimide (3.00 g, 9.79 mmol) and hydrazinemonohydorate (0.95 mL, 19.6 mmol) in EtOH (40 mL) was stirred at room temperature for 1.5 h. The reaction mixture was filtered followed by the removal of solvent. The crude product was purified by column chromatography (NH, EtOAc) to yield trans-3-(3-pyridyl)cyclohexylamine (1.08 g, 60%) 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-74dd4d4486cf4557ae5649deffc813e6
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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