Hydrochloric Acid → HCID 178505567, compound

HRID 2287423Notes

Reaction equation

HRID 2287423 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[NH:16][C:17]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:17]2[NH:16][C:15]([CH:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)=[N:19][C:18]=2[C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451796HCID 178451796, compound

Product 1

HCID 178505567HCID 178505567, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride gas was bubbled through a stirred solution of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.36 mmol,0.15 g) in ethyl acetate (5 mL) for 0.5 h. The solvent was then evaporated under reduced pressure and the residue diluted with saturated sodium bicarbonate (50 mL). The resulting suspension was extracted with methylene chloride (5×20 mL), the organic layers combined, washed with brine, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure. The resulting material was crystallized from diethyl ether to give 30 mg of the title compound as a white powder.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. additionthe residue diluted with saturated sodium bicarbonate (50 mL)
  3. extractionThe resulting suspension was extracted with methylene chloride (5×20 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent evaporated under reduced pressure
  7. customThe resulting material was crystallized from diethyl ether

Sources & evidence

ORD record
ord-c560ab39ad454ebcba7c32ab60f50246
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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