3-Nitro-4-piperidin-1-ylpyridine → 4-(Piperidin-1-yl)pyridin-3-amine

HRID 408450Notes

Reaction equation

HRID 408450 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([O-])=O>C(O)C.[Pd]>[N:10]1([C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH2:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 35076693-Nitro-4-piperidin-1-ylpyridine

Product 1

HCID 3486384-(Piperidin-1-yl)pyridin-3-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-nitro-4-(piperidin-1-yl)pyridine (1.0 equiv.) in ethanol, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 15 hours. At this time the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding 4-(piperidin-1-yl)pyridin-3-amine (93%) as an oil. LCMS (m/z): 178.0 (MH+); LC Rt=1.68 min. 1H NMR (CDCl3): δ 8.01 (s, 1H), 7.96 (d, J=5.4, 1H), 6.78 (d, J=5.1, 1H), 3.64-3.74 (m, 2H), 2.86-2.94 (m, 4H), 1.66-1.78 (m, 4H), 1.58-1.64 (m, 2H).

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with methanol
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-2952121e880b4422b9dada26b685122f
Source dataset
uspto-grants-2014_06
Patent number
US08759338B2

Reaction notes

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