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]1To a suspension of 2-[1-(phenylmethyl)-3pyrrolidinyl]pyridine (7.15 g, 30.0mmol) 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 retool) in water (30 mL). The mixture was heated at reflux for 30 minutes, allowed tocool to room temperature, and filtered. The filtrate was concentrated underreduced 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, driedover anhydrous potassium carbonate, and concentrated to a yellow oil. This crude product was chromatographed (silica gel, chloroform-methanol-ammonia75:25:5) to give the title compound (3.33 g, 75%) as a faint yellow liquid.
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