1-tert-Butyl-4-piperidone → 1-tert-Butylpiperidin-4-amine

HRID 1035968Notes

Reaction equation

HRID 1035968 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+:15]>CO.O.[Pd]>[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:15])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 738401-tert-Butyl-4-piperidoneHCID 2723923Ammonium formate

Product 1

HCID 177504011-tert-Butylpiperidin-4-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-tert-butylpiperidin-4-one (5.0 g) in methanol (100 mL) and water (10 mL) was added ammonium formate (20.3 g) and 0.5 g of Pd/C (10%). The mixture was stirred overnight. The mixture was filtered and the filtrate was concentrated under vacuum and the residue was diluted with ethyl acetate (500 mL) and washed with water and brine. After drying over Na2SO4 and filtration, the solvent was evaporated under vacuum to provide the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionthe residue was diluted with ethyl acetate (500 mL)
  4. washwashed with water and brine
  5. dry with materialAfter drying over Na2SO4 and filtration
  6. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-a28e3f635fd24d04981eb23742ad0539
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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