4-[3-(Methyloxy)-4-nitrophenyl]-1-(2-methylpropyl)-1,2,3,6-tetrahydropyridine → {2-(Methyloxy)-4-[1-(2-methylpropyl)-4-piperidinyl]phenyl}amine

HRID 419527Notes

Reaction equation

HRID 419527 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CO.[Pd].[C]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([CH3:20])[CH3:21])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 1

HCID 594528154-[3-(Methyloxy)-4-nitrophenyl]-1-(2-methylpropyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 59452706{2-(Methyloxy)-4-[1-(2-methylpropyl)-4-piperidinyl]phenyl}amineYield 9,891.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[3-(methyloxy)-4-nitrophenyl]-1-(2-methylpropyl)-1,2,3,6-tetrahydropyridine (1.90 g, 0.0655 mmol) in MeOH was added 10% Pd/carbon (0.800 g). The resulting suspension was stirred at rt under 60 psi H2 overnight. Subsequent filtration through celite and concentration under reduced pressure afforded {2-(methyloxy)-4-[1-(2-methylpropyl)-4-piperidinyl]phenyl}amine (1.7 g, 89% yield) as a dark brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.63 (s, 1H), 6.51 (s, 2H), 4.44 (s, 2H), 3.72 (s, 3H), 2.87 (d, J=11.36 Hz, 2H), 2.22-2.33 (m, J=11.82, 7.79, 4.03, 3.85 Hz, 1H), 2.01 (d, J=7.33 Hz, 2H), 1.88 (td, J=11.55, 2.57 Hz, 2H), 1.75 (dt, J=13.66, 6.92 Hz, 1H), 1.60-1.67 (m, 2H), 1.56 (dd, J=12.28, 3.48 Hz, 2H), 0.84 (d, J=6.60 Hz, 6H).

Workup

  1. filtrationSubsequent filtration
  2. concentrationthrough celite and concentration under reduced pressure

Sources & evidence

ORD record
ord-47c674cd046840fbadf8eecc958a4074
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…