Ammonium formate → 2-(Pyrrolidin-3-yl)pyridine

HRID 54469Notes

Reaction equation

HRID 54469 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:9]2)C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 109556222-(1-Benzylpyrrolidin-3-yl)pyridine

Product 1

HCID 50139382-(Pyrrolidin-3-yl)pyridineYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine (7.15 g, 30.0 mmol) and 10% palladium on charcoal catalyst (1.90 g) in methanol (120 mL) was added dropwise a solution of ammonium formate (7.57 g, 120 mmol) in water (30 mL). The mixture was heated at reflux for 30 minutes, allowed to cool to room temperature, and filtered. The filtrate was concentrated under reduced pressure, the residue was taken up in water (10 mL), and the solution was made basic with concentrated ammonia and extracted with dichloromethane (4×15 mL). The organic extracts were combined, dried over anhydrous potassium carbonate, and concentrated to a yellow oil. This crude product was chromatographed (silica gel, chloroform-methanol-ammonia 75:25:5) to give the title compound (3.33 g, 75%) as a faint yellow liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionextracted with dichloromethane (4×15 mL)
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated to a yellow oil
  8. customThis crude product was chromatographed (silica gel, chloroform-methanol-ammonia 75:25:5)

Sources & evidence

ORD record
ord-d9df612e9c6a45d9938703ca0ca2de1f
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Reaction notes

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