1-(1-Benzylpiperidin-4-yl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole → 1-(1-Formyl-4-piperidinyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)imidazole

HRID 1858431Notes

Reaction equation

HRID 1858431 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[N:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=[O:33].CO>[Pd]>[CH:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[N:16]=[CH:15]2)[CH2:12][CH2:13]1)=[O:33]

Participants

4

Reactant 2

HCID 113504541-(1-Benzylpiperidin-4-yl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazoleHCID 18963719Formic acid methanol2×

Product 1

HCID 224641231-(1-Formyl-4-piperidinyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)imidazole

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-(1-Benzylpiperidin-4-yl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole (100 mg; prepared in Example 40) was dissolved in 10% formic acid/methanol under argon and palladium black (100 mg) mixed in 10% formic acid/methanol was added. The reaction was stirred under argon at room temperature for sixteen hours. The reaction mixture was evaporated and the residue mixed in H2O/ethyl acetate and the pH taken to 10. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were evaporated and the residue was flash chromatographed (silica gel/methylene chloride/methanol) to yield the title compound, an off-white solid. ES (+) MS m/e=351 (MH+)

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. additionthe residue mixed in H2O/ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with ethyl acetate
  6. customThe combined organic layers were evaporated
  7. customchromatographed (silica gel/methylene chloride/methanol)

Sources & evidence

ORD record
ord-98a7a65979fb4deaa5260943a1e28ab3
Source dataset
uspto-grants-2000_11
Patent number
US06150557

Reaction notes

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