Tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

HRID 1989050Notes

Reaction equation

HRID 1989050 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]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[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 53415310Tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateYield 105.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(4-amino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.35 g, 1.2 mmol) (as prepared in the previous step) in methanol was hydrogenated over 10% Pd/C at 20 psi for 1 h. The solution was filtered and concentrated to give 0.35 g (100%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 6.85 (d, J=8.3 Hz, 2H), 6.50 (d, J=8.3 Hz, 2H), 4.81 (s, 2H), 4.012 (m, 2H), 3.85 (br, 2H), 2.44 (m, 1H), 2.66 (m, 2H), 1.42 (m, 11H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-61f7e82ff79f430c985477764e0bf10f
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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