Ammonium formate → 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

HRID 8723Notes

Reaction equation

HRID 8723 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)[CH:15]=[N:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:19]1([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]([N:14]2[C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[N:16]=[CH:15]2)[CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219836255-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Product 1

HCID 219836441-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridineYield 32.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 17a (500 mg, 1.6 mmol), ammonium formate (1.0 g), and 700 mg 5% Pd/C (50% with water) in 80% aqueous methanol was heated at reflux for 12 hr, and then allowed to reach ambient temperature. The catalyst was removed by filtration through Celite®. The filtrate was evaporated in vacuo. Purification by silica gel chromatography provided 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (110 mg) 18a as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hr
  3. customto reach ambient temperature
  4. customThe catalyst was removed by filtration through Celite®
  5. customThe filtrate was evaporated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-b8fb1c319e5948b89f7e69697197210e
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Reaction notes

Loading…