Ammonia → Ammonia

HRID 1829176Notes

Reaction equation

HRID 1829176 reaction equation
[NH3:1].[C:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)(=[O:4])[CH3:3]>CO.[OH-].[Pd+2].[OH-]>[NH3:5].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:1])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 118159051-Acetylpiperidin-2-one

Product 2

HCID 222AmmoniaHCID 49624771-(4-Aminopiperidin-1-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

0.88 Ammonia (85 ml) was added to a solution of N-acetylpiperidone (15 g, 106 mmol) in methanol (120 ml), followed by palladium hydroxide (2 g) and the mixture hydrogenated at room temperature and 60 psi for 18 hours. The reaction mixture was filtered through Arbocel®, the filtrate concentrated under reduced pressure and the residue azeotroped with toluene to give a yellow oil. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (96:3.5:0.5 to 84:14:2) to afford the title compound as a clear oil, 9.6 g.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue azeotroped with toluene
  4. customto give a yellow oil
  5. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-3aeb0bdf566a4404b998247c8e514b62
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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