Ammonium formate → 4-(1-Acetylpiperidin-4-yl)furo[3,2-c]pyridine

HRID 2184803Notes

Reaction equation

HRID 2184803 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:15]3[CH:16]=[CH:17][O:18][C:14]=3[CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:15]3[CH:16]=[CH:17][O:18][C:14]=3[CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 183997764-(1-Acetyl-1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridine

Product 1

HCID 183997294-(1-Acetylpiperidin-4-yl)furo[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

0.7 g of Pd/C (10%) is added to a solution of 3.4 g of the product obtained in Step C and 4.4 g of ammonium formate in 150 ml of anhydrous methanol under a stream of argon. After refluxing for 45 minutes, the reaction mixture is cooled, 4.4 g of ammonium formate 5 and 0.2 g of Pd/C (10%) are added, and the reaction mixture is then heated at reflux for 30 minutes. After returning to ambient temperature, filtration over Celite and concentration under reduced pressure, the residue is taken up in water and then extracted with dichloromethane. The expected product is isolated by extraction, drying, filtration and concentration under reduced pressure.

Workup

  1. temperatureAfter refluxing for 45 minutes
  2. temperaturethe reaction mixture is cooled
  3. temperaturethe reaction mixture is then heated
  4. temperatureat reflux for 30 minutes
  5. customAfter returning to ambient temperature
  6. filtrationfiltration
  7. concentrationover Celite and concentration under reduced pressure
  8. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-ea629e2966e64f38bae43c969242f85d
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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