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

HRID 1434607Notes

Reaction equation

HRID 1434607 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1[NH:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)([O-])=O.[CH3:25]O>[Pd]>[NH:15]1[CH2:14][CH2:13][CH:12]([N:11]2[C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[N:1]=[CH:25]2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 887MethanolHCID 57935996Tert-butyl 4-[(4-nitro-1-oxidopyridin-3-yl)amino]piperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of tert-butyl 4-[(4-nitro-1-oxidopyridin-3-yl)amino]piperidine-1-carboxylate (4 g) in methanol (100 ml) was added 10% palladium on carbon (50 mg) and the mixture was placed under a hydrogen atmosphere (60 psi) for 48 hours. The mixture was filtered through Celite and evaporated to dryness to give the title compound as a solid, which was used without further purification. Yield 3.21 g. MS 293 (M+H).

Workup

  1. customfor 48 hours
  2. filtrationThe mixture was filtered through Celite
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-7477aa79154742518fa27c30b5e345b6
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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