Ammonium formate → HCID 23627639, compound

HRID 1663238Notes

Reaction equation

HRID 1663238 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][CH2:23][CH2:24][N:25]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:25]1[CH2:24][CH2:23][N:22]=[C:21]1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67436113HCID 67436113, compound

Product 1

HCID 23627639HCID 23627639, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 1-benzyl-4-[4-(4,5-dihydro-1H-imidazol-2-yl)-benzylidene]-piperidine (0.1 g, 0.3 mmol) in ethanol (20 mL), ammoniumformate (0.19 g, 3 mmol) and 10% Pd/C (20 mg) were added ad the mixture was refluxed for 8 hours. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The remaining crude material was purified by column chromatography using basic aluminum oxide (150 mesh, Aldrich) as adsorbent and 10% methanol in chloroform as eluent to yield 68 mg (92%) of the title compound.

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe remaining crude material was purified by column chromatography

Sources & evidence

ORD record
ord-aca259d1ac6b4f439ea753a46061e867
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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