Potassium Carbonate → HCID 86613928, compound

HRID 1811429Notes

Reaction equation

HRID 1811429 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH:15]3[O:19]CCO3)[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:20].[CH2:21]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:21]([CH:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[C:10]([CH:15]=[O:19])[C:9]=3[CH2:8][CH2:7][C:6]2=[O:20])[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 665970461-(3-Bromopropyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 86613928HCID 86613928, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Bromopropyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (790 mg, 2.32 mmol), 4-benzylpiperidine (0.49 ml, 2.79 mmol) and potassium carbonate (142 mg, 1.03 mmol) were added to acetonitrile (15 ml), followed by heating under reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered to remove the insoluble matter. The solid was washed with acetonitrile, and the filtrate and washing were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→ethyl acetate:methanol=50:1). The purified product was concentrated under reduced pressure, and the residue was dissolved in acetone (15 ml). p-Toluenesulfonic acid monohydrate (368 mg) was added, and the resulting mixture was heated under reflux for 2 hours. An aqueous solution of potassium carbonate was added to the reaction mixture, followed by concentration under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain 672 mg (yield: quantitative) of 1-[3-(4-benzylpiperidin-1-yl)propyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a colorless oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. filtrationthe reaction mixture was filtered
  4. customto remove the insoluble matter
  5. washThe solid was washed with acetonitrile
  6. washthe filtrate and washing
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→ethyl acetate:methanol=50:1)
  9. concentrationThe purified product was concentrated under reduced pressure
  10. dissolutionthe residue was dissolved in acetone (15 ml)
  11. additionp-Toluenesulfonic acid monohydrate (368 mg) was added
  12. temperaturethe resulting mixture was heated
  13. temperatureunder reflux for 2 hours
  14. additionAn aqueous solution of potassium carbonate was added to the reaction mixture
  15. concentrationfollowed by concentration under reduced pressure
  16. additionWater was added to the residue, and extraction with dichloromethane
  17. washThe organic layer was washed with a saturated sodium chloride solution
  18. dry with materialdried over anhydrous sodium sulfate
  19. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c86541fdc4f1404a91fc2bb494df6769
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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