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

HRID 1740575Notes

Reaction equation

HRID 1740575 reaction equation
C(N1CCC([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)CC1)C1C=CC=CC=1.[CH:32]([OH:34])=O.CO>[Pd]>[CH:32]([N:22]1[CH2:23][CH2:24][CH2:19][CH2:20][CH:21]1[C:15]1[NH:14][C:18]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[C:17]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[N:16]=1)=[O:34]

Participants

4

Reactant 2

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

Product 1

HCID 86754653(1-Formyl 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.

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

Sources & evidence

ORD record
ord-625e874e5525466ba58cb7d0fb4a567c
Source dataset
uspto-grants-1999_10
Patent number
US05969184

Reaction notes

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