Acetic Acid → 1-[4-(Aminomethyl)piperidin-1-yl]-3,3-dimethylbutan-2-one

HRID 965792Notes

Reaction equation

HRID 965792 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3](=[O:23])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6]1.C(O)(=O)C>[Pd].C(O)C>[NH2:12][CH2:11][CH:8]1[CH2:7][CH2:6][N:5]([CH2:4][C:3](=[O:23])[C:2]([CH3:24])([CH3:1])[CH3:25])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86759854Benzyl [1-(3,3-dimethyl-2-oxobutyl)piperidin-4-yl]methylcarbamate

Product 1

HCID 223132621-[4-(Aminomethyl)piperidin-1-yl]-3,3-dimethylbutan-2-oneYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl [1-(3,3-dimethyl-2-oxobutyl)piperidin-4-yl]methylcarbamate (Step 1, 9.6 g, 27.7 mmol), 5% palladium on carbon (1.2 g) and acetic acid (4 mL) in ethanol (70 mL) was stirred at room temperature for 23 h under hydrogen atmosphere. Palladium on carbon was removed by filtration through a pad of Celite and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with aqueous ammonia and extracted with ethyl acetate (5×50 mL). After dried over magnesium sulfate, removal of solvent gave the title compound (2.7 g, 46%) as a yellow oil.

Workup

  1. customPalladium on carbon was removed by filtration through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous ammonia
  5. extractionextracted with ethyl acetate (5×50 mL)
  6. dry with materialAfter dried over magnesium sulfate, removal of solvent

Sources & evidence

ORD record
ord-aa4e061e610541b5831e5c153efcbc5d
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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