Potassium Carbonate → 3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

HRID 1434606Notes

Reaction equation

HRID 1434606 reaction equation
F[C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.[C:26](=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:4]1[CH2:5][CH2:6][CH:7]([N:8]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:26]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 579359853-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-fluoro-4-nitropyridine-N-oxide (3.46 g) and tert-butyl 4-aminopiperidine-1-carboxylate (2.745 g) in acetonitrile (150 ml) was added anhydrous potassium carbonate (2.74 g) and the resulting mixture was refluxed for 8 hours. The mixture was filtered and washed well with dichloromethane. The organics were concentrated to dryness and the residue was purified by column chromatography eluting with a mixture of ethyl acetate and dichloromethane (1:1) to give the titled compound as a yellow solid. Yield 3.25 g. NMR (d6 DMSO) 1.4 (s, 9H), 1.5 (M, 2H), 1.9 (m, 2H), 2.95 (m, 2H), 3.9 (m, 3H), 7.5 (dd, 1H), 7.85 (d, 1H), 8.05 (d, 1H) 8.4 (d, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 8 hours
  2. filtrationThe mixture was filtered
  3. washwashed well with dichloromethane
  4. concentrationThe organics were concentrated to dryness
  5. customthe residue was purified by column chromatography
  6. washeluting with a mixture of ethyl acetate and dichloromethane (1:1)

Sources & evidence

ORD record
ord-b277e13a74e84223867d842b6bac93c4
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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