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

HRID 2367769Notes

Reaction equation

HRID 2367769 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: Mass spectrum (ESI, m/z): Calcd. for C16H24N2O2, 277.2 (M+H). found 277.1.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ea3689f7acaa4ad7a6d6ed480d576f74
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

Loading…