1-(1-Benzyl-piperidin-4-yl)-5-fluoro-2-pentafluoroethyl-1H-benzoimidazole → 1-(Piperidin-4-yl)-5-fluoro-2-pentafluoroethyl-1 H-benzoimidazole

HRID 1371505Notes

Reaction equation

HRID 1371505 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[N:16]=[C:15]2[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[N:16]=[C:15]2[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 179896571-(1-Benzyl-piperidin-4-yl)-5-fluoro-2-pentafluoroethyl-1H-benzoimidazole

Product 1

HCID 179896551-(Piperidin-4-yl)-5-fluoro-2-pentafluoroethyl-1 H-benzoimidazoleYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.7 g 1-(1-Benzyl-piperidin-4-yl)-5-fluoro-2-pentafluoroethyl-1H-benzoimidazole were dissolved in 100 ml methanol and hydrogenated with 2 g Pd/C (10%) at 50° C. and 60 psi for 2 h. The catalyst was removed and the filtrate was evaporated. The residue was crystallized with diisopropyl ether and petrol ether 1:1 to yield 3.9 g beige crystals (mp. 177–178° C.).

Workup

  1. customThe catalyst was removed
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized with diisopropyl ether and petrol ether 1:1

Sources & evidence

ORD record
ord-8acd6fef4b4545598c7ea5d270b38fdc
Source dataset
uspto-grants-2007_01
Patent number
US07157471B2

Reaction notes

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