2-Nitro-5-(piperidin-1-yl)pyridine → 5-(Piperidin-1-yl)pyridin-2-amine

HRID 586523

Reaction equation

HRID 586523 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Ni]>[N:10]1([C:7]2[CH:8]=[N:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 29279612-Nitro-5-(piperidin-1-yl)pyridine

Product 1

HCID 112982775-(Piperidin-1-yl)pyridin-2-amineYield 121.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6′-Nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (4.69 g, 22.6 mmol) was dissolved in THF (100 mL) to which Raney Nickel (1.08 g) was added. The reaction was shaken under a hydrogen atmosphere (50 psi) for 4 hours. The catalyst was removed by filtration and the solvent evaporated to give 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine as a purple solid (4.86 g, 85.7%). 1H NMR δ (400 MHz, CDCl3) 7.76 (d, J=2.4 Hz, 1H), 7.19 (dd, J=2.9, 8.8 Hz, 1H), 6.47 (dd, J=0.7, 8.8 Hz, 1H), 4.18 (s, 2H), 2.97 (m, 4H), 1.71 (m, 4H), 1.53 (m, 2H).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-e5a6b18bcc794be5a1be8160620afea6
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Linked notes

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