反应详情

A solution of 9.138 g (29.73 mmol) of N-(6-phenylhexyl)phthalimide and 2.16 ml (44.6 mmol) of hydrazine monohydrate in 100 ml of ethanol was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude 6-phenylhexylamine was dissolved in 100 ml of methanol; 2.86 g (29.7 mmol) of 3-furaldehyde was added, followed by stirring at room temperature for 0.5 hours, after which 2.25 g (59.5 mmol) of sodium borohydride was added under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to yield the desired product.

1. extractionextracted with dichloromethane 3 times
2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
3. distillationthe solvent was distilled off under reduced pressure
4. dissolutionThe resulting crude 6-phenylhexylamine was dissolved in 100 ml of methanol
5. temperaturecooling
6. stirringby stirring at room temperature for 1 hour
7. extractionextracted with dichloromethane 3 times
8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)