Hydrochloric Acid → HCID 17989653, compound

HRID 1371508Notes

Reaction equation

HRID 1371508 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][C:25]([F:28])([F:27])[F:26])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>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[CH2:24][C:25]([F:28])([F:26])[F:27])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 17989658HCID 17989658, compound

Product 1

HCID 17989653HCID 17989653, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11.9 g 1-(1-Benzyl-piperidin-4-yl)-5-fluoro-2-(2,2,2-trifluoroethyl)-1H-benzoimidazole×HCl in 200 ml methanol was hydrogenated with 2.5 g Pd/C (10%) as catalyst at 40° C. and 4 bar for 2.5 h. After the reaction the catalyst was removed and the solvent was evaporated. The residue was dissolved in 200 ml water, treated with 4 N NaOH, extracted 2× with ethyl acetate, and the organic layers were extracted 2× with water and dried with MgSO4. Evaporation of the solvent yielded 6.1 g beige crystals (mp. 135° C.).

Workup

  1. customAfter the reaction the catalyst
  2. customwas removed
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in 200 ml water
  5. additiontreated with 4 N NaOH
  6. extractionextracted 2× with ethyl acetate
  7. extractionthe organic layers were extracted 2× with water
  8. dry with materialdried with MgSO4
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b8dce69a6b6f47d6aa85280b610436c9
Source dataset
uspto-grants-2007_01
Patent number
US07157471B2

Reaction notes

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