1-(1-Benzyl-piperidin-4-yl)-2-ethyl-5-fluoro-1H-benzimidazole → 2-Ethyl-5-fluoro-1-piperidin-4-yl-1H-benzimidazole

HRID 2240280Notes

Reaction equation

HRID 2240280 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[CH2:24][CH3:25])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH2:24]([C:15]1[N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:18]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=2[N:16]=1)[CH3:25]

Participants

4

Reactant 1

HCID 585995231-(1-Benzyl-piperidin-4-yl)-2-ethyl-5-fluoro-1H-benzimidazole

Product 1

HCID 585995212-Ethyl-5-fluoro-1-piperidin-4-yl-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(1-Benzyl-piperidin-4-yl)-2-ethyl-5-fluoro-1H-benzimidazole (6.4 g) in methanol (100 ml) was hydrogenated with Pd/C (10%, 1.5 g) at room temperature for 8 h. The catalyst was removed and the filtrate was evaporated and dissolved in ethanol. The solution was acidified with conc. HCl(aq) and recrystallised by the addition of acetone. This yielded 5.3 g of the title compound as colourless crystals.

Workup

  1. customThe catalyst was removed
  2. customthe filtrate was evaporated
  3. dissolutiondissolved in ethanol
  4. customrecrystallised by the addition of acetone

Sources & evidence

ORD record
ord-ba2e01b289a04109b1e2123921cb8f20
Source dataset
uspto-grants-2010_05
Patent number
US07723360B2

Reaction notes

Loading…