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

HRID 69872Notes

Reaction equation

HRID 69872 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-])=O.[H][H]>C(O)C.[Pd]>[N:11]1([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 147359134-Nitro-3-(piperidin-1-yl)pyridine 1-oxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 690473683-(Piperidin-1-yl)pyridin-4-amineYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

To a solution of 4-nitro-3-(piperidin-1-yl)pyridine 1-oxide (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 LC/MS analysis indicated that the nitro was reduced to the amine, but the N-oxide was remaining. More 10% palladium on carbon (0.2 eq.) was added and the mixture was resubmitted to a balloon atmosphere of hydrogen. After stirring for 24 hours, more 10% palladium on carbon (0.2 eq.) was added and the mixture was resubmitted to a balloon atmosphere of hydrogen. After stirring for an additional 3 days the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding 3-(piperidin-1-yl)pyridin-4-amine (73%). LCMS (m/z): 178.0 (MH+); LC Rt=1.66 min.

Workup

  1. stirringAfter stirring for 24 hours
  2. stirringAfter stirring for an additional 3 days the mixture
  3. filtrationwas filtered through a pad of celite
  4. washeluting with methanol
  5. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-88ea49dceea6479bb3324053034ea6bf
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

Loading…