Sodium hydride → 2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one

HRID 887766Notes

Reaction equation

HRID 887766 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]1[N:14]=[C:13]([C:15](OC)=[O:16])[C:12]([CH2:19][CH2:20]C(OC)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>O1CCCC1.CO>[CH2:1]([N:8]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:9]1[N:14]=[C:13]2[C:15](=[O:16])[CH2:20][CH2:19][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59145865Methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylate

Product 1

HCID 591459342-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-oneYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylate (2.02 g, 4.83 mmol) and 60% sodium hydride (386 mg, 9.65 mmol) in tetrahydrofuran (48 mL) was added methanol (1 drop), and the mixture was heated under reflux for 1.5 hr. The reaction solution was concentrated to dryness, 12M hydrochloric acid (24 mL) was added, and the mixture was stirred at 110° C. for 15 min. The reaction solution was diluted with ethyl acetate, neutralized with saturated aqueous sodium hydrogen carbonate solution, and washed with saturated brine. This was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (1.17 g, yield 74%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. concentrationThe reaction solution was concentrated to dryness, 12M hydrochloric acid (24 mL)
  4. additionwas added
  5. additionThe reaction solution was diluted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialThis was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-51a4b1500fb1420e9dce3ffe757e6f9d
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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