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Under nitrogen in a dry round bottom flask fitted with a condensor and magnetic stir bar were placed 2-(4methyl-1-piperazinyl)-benzaldehyde (0.152 g, 0.75 g, 0.75 mmol), oxindole (0.104 g, 0.78 mmol) pyrrolidine (62 μL) and ethanol (7.0 mL). The mixture was heated to reflux for 16 hours, cooled and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer was washed with saturated aqueous sodium chloride (NaCl), dried over magnesium sulfate (MgSO4)1, filtered and absorbed onto 437 mg of silica gel. Elution with ethyl acetate (EtOAc) (125 mL), 1% methanol (CH3OH) in EtOAc (100 mL), 2% CH3OH in EtOAc (100 mL) and 4% CH3OH+1% triethylamine (Et3N) In EtOAc (50 mL) gave 280 mg of a yellow solid. Recrystallization from hot CH3OH gave the title product, m.p. 226-2280° C.

1. customUnder nitrogen in a dry round bottom flask fitted with a condensor and magnetic stir bar
2. temperatureThe mixture was heated
3. temperatureto reflux for 16 hours
4. temperaturecooled
5. customevaporated under reduced pressure
6. customThe residue was partitioned between ethyl acetate and water
7. washthe organic layer was washed with saturated aqueous sodium chloride (NaCl)
8. dry with materialdried over magnesium sulfate (MgSO4)1
9. filtrationfiltered
10. customabsorbed onto 437 mg of silica gel
11. washElution with ethyl acetate (EtOAc) (125 mL), 1% methanol (CH3OH) in EtOAc (100 mL), 2% CH3OH in EtOAc (100 mL)