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To 70 mL of a solution of 1-benzyl-4-(pyrrolidin-1-yl)-1,2,3,6-tetrahydropyridine in benzene was added dropwise a solution 13 g of 4-bromoacetyl pyridine bromohydride in 150 mL of benzene at 0° C. over 1 hour, followed by stirring at 0° C. for 1 hour and then at room temperature for 15 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol), and to the obtained 1.86 g of 1-benzyl-3-[2-oxo-2-(pyridin-4-yl)ethyl]piperidine-4-one were added 20 mL of acetic acid and 605 mg of ammonium acetate, followed by heating and refluxing for 1 hour. The reaction mixture was cooled to room temperature and the pH was adjusted to about 9 with a 10% aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol) to obtain 1.26 g of 5-benzyl-2-(pyridin-4-yl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine.

1. waitat room temperature for 15 hours
2. extractionfollowed by extraction with ethyl acetate
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)
6. additionto the obtained 1.86 g of 1-benzyl-3-[2-oxo-2-(pyridin-4-yl)ethyl]piperidine-4-one were added 20 mL of acetic acid and 605 mg of ammonium acetate
7. temperatureby heating
8. temperaturerefluxing for 1 hour
9. temperatureThe reaction mixture was cooled to room temperature
10. extractionfollowed by extraction with ethyl acetate
11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)