Hydrochloric Acid → HCID 68676595, compound

HRID 1992108Notes

Reaction equation

HRID 1992108 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:24][CH2:25][N:26]2[C@H:31]3[CH2:32][CH2:33][C@@H:27]2[CH2:28][CH:29]([N:34]2[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[N:36]=[C:35]2[CH3:43])[CH2:30]3)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:44]>[Pd].CO>[ClH:44].[ClH:44].[CH3:43][C:35]1[N:34]([CH:29]2[CH2:28][CH:27]3[N:26]([CH2:25][CH2:24][C:11]4([C:14]5[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[CH:15]=5)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58728371HCID 58728371, compound

Product 1

HCID 68676595HCID 68676595, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[(1R,5S)-8-(2-{1-benzyl-4-[3-(trifluoromethyl)phenyl]piperidin-4-yl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole (0.2 g, 0.34 mmol), 1N hydrochloric acid (0.34 mL) and 10% Palladium on carbon (50 mg) in methanol (10 mL) was hydrogenated overnight at rt and atmospheric pressure. The mixture was filtered through celite and concentrated to give 2-methyl-1-[8-(2-{4-[3-(trifluoromethyl)phenyl]piperidin-4-yl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-1H-benzimidazole dihydrochloride as a solid (0.15 g, 89%) that was used without further purification.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c672621bbdf049ffbcbb01a2d22d9fd5
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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