HCID 67067334, compound → HCID 67067247, compound

HRID 1009356Notes

Reaction equation

HRID 1009356 reaction equation
C[O:2][C:3](OC)([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[CH2:4][N:5]1[CH2:10][CH2:9][CH2:8]/[C:7](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]3)=[C:14]([O:24][CH3:25])[CH:13]=2)/[C:6]1=[O:26]>Cl>[CH3:25][O:24][C:14]1[CH:13]=[C:12](/[CH:11]=[C:7]2/[C:6](=[O:26])[N:5]([CH2:4][C:3](=[O:2])[C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH2:10][CH2:9][CH2:8]/2)[CH:17]=[CH:16][C:15]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1

Participants

3

Reactant 1

HCID 67067334HCID 67067334, compound

Product 1

HCID 67067247HCID 67067247, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated hydrochloric acid (10 mL) was added to 1-(2,2-dimethoxy-2-pyridin-4-ylethyl)-3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}piperidin-2-one (580 mg), and the mixture was stirred at 50° C. for four hours. After confirming that the raw materials disappeared, the reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate=1:2) to obtain 346.2 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. additionSaturated sodium bicarbonate water and ethyl acetate were added to the resulting residue
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-3693230b6ec6488c9ef4f2cba357c418
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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