Diethylamine → Tert-butyl 4-(diethylamino)piperidine-1-carboxylate

HRID 402707Notes

Reaction equation

HRID 402707 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>CO.[Pd]>[CH2:15]([N:17]([CH2:18][CH3:19])[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)[CH3:16]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 63788695Tert-butyl 4-(diethylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 0.025 mol) and diethylamine (9.1 mL, 0.090 mol) in methanol (40 mL), 10% palladium on carbon (0.50 g) was added at ambient temperature. The reaction mixture was agitated under a hydrogen atmosphere at ambient temperature for 16 h. Palladium on carbon was removed by filtration with Celite and the solvent was removed under reduced pressure, then the residue was purified by chromatography on silica gel(dichloromethane/methanol) to afford tert-butyl 4-(diethylamino)piperidine-1-carboxylate as solid (6.1 g, y. 95%).

Workup

  1. customPalladium on carbon was removed by filtration with Celite
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by chromatography on silica gel(dichloromethane/methanol)

Sources & evidence

ORD record
ord-ccc741b1440d457ebb737e2b9047253c
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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