Ammonium formate → 4-((1H-Benzimidazol-2-yl)methyl)piperidine HCOOH

HRID 1386785Notes

Reaction equation

HRID 1386785 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH:24]([O-:26])=[O:25].[NH4+]>[Pd].CO>[NH:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1.[CH:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 140128452-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole

Product 1

HCID 1317228154-((1H-Benzimidazol-2-yl)methyl)piperidine HCOOHYield 65.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 66 mg of 1-benzyl-4-((1H-benzimidazol-2-yl)methyl)piperidine (from EXAMPLE 164, Step A), 66 mg of 10% palladium on carbon and 68 mg of ammonium formate in 10 mL of MeOH was heated at reflux for 3 h. The mixture was cooled and filtered through celite. Concentration afforded 37 mg of the title compound as a foamy solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationConcentration

Sources & evidence

ORD record
ord-3d593a258b2447488d6e622e0c03f342
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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