4-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

HRID 1267118Notes

Reaction equation

HRID 1267118 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 537487374-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(4-benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.27 g) in EtOH (10 mL) containing Pd/C 10% (50 mg) was hydrogenated at room temperature. After 1 hour, the catalyst was removed by filtration and the filtrate was evaporated under reduced pressure to give the title compound (0.18 g) as a pale pink oil.

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8533461ffa7942efbaec63279dcd6cd2
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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