2-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine → 2-Oxo-3-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine

HRID 20077

Reaction equation

HRID 20077 reaction equation
[O:1]=[C:2]1[N:10]([CH:11]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12]2)[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[NH:3]1>CO.[OH-].[OH-].[Pd+2]>[O:1]=[C:2]1[N:10]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[NH:3]1

Participants

4

Reactant 1

HCID 222931702-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine

Product 1

HCID 222931682-Oxo-3-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-c]pyridineYield 85.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine (0.5 g, 1.6 mmol) in methanol (250 mL) was shaken with 20% Pd(OH)2 under a hydrogen atmosphere for 48 h at room temperature. The reaction was filtered and concentrated to give the title compound as a white solid (0.3 g). MS 219 (M+1).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dab530cccde34b519cf1553538d26a62
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Linked notes

Loading…