Ammonium formate → HCID 18506994, compound

HRID 1992049Notes

Reaction equation

HRID 1992049 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([N:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]1[CH3:25])[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[CH:9]12[NH:8][CH:13]([CH2:14][CH2:15]1)[CH2:12][CH:11]([N:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]1[CH3:25])[CH2:10]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18506983HCID 18506983, compound

Product 1

HCID 18506994HCID 18506994, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2.2 g (6.65 mmol) 1-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole was dissolved in 150 ml ethanol and 2.09 g (33.23 mmol) ammonium formate and 0.4 g palladium hydroxide (20% on carbon) were added. The mixture was refluxed for 2.5 hrs. The mixture was cooled to ambient temperature and filtered through celite. The solvent was removed under reduced pressure and the crude product was purified by column chromatography CH2Cl:CH3OH:NH4OH (95:5:0.5) to afford 1.06 g of the desired product as a solid.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hrs
  2. filtrationfiltered through celite
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was purified by column chromatography CH2Cl:CH3OH:NH4OH (95:5:0.5)

Sources & evidence

ORD record
ord-fdcd5d253b254ebf9f7c0f7557ebb199
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…