5-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine → 5-(1-Methylpiperidin-4-yl)pyridin-2-amine

HRID 1918860Notes

Reaction equation

HRID 1918860 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-])=O)=[N:12][CH:13]=2)[CH2:4][CH2:3]1>[Pd].CCO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 580442465-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

Product 1

HCID 580438205-(1-Methylpiperidin-4-yl)pyridin-2-amineYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a hydrogenation bottle, 130a (1.25 g, 5.73 mmol), EtOH (100 mL), 10% Pd/C (304 mmol, 0.286 mmol) were added. The mixture was hydrogenated at 55 psi for 2 hrs, filtered through celite, and washed with MeOH (20 mL). The solvent was removed in vacuo and off-white solids were obtained as 5-(1-methylpiperidin-4-yl)pyridin-2-amine 130b (1.13 g, 100%).

Workup

  1. filtrationfiltered through celite
  2. washwashed with MeOH (20 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-10094f850a1c4d94a12e395ff209c55c
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…