Triethylamine → Phthalimide

Temperature

120 °C

4-Methylimidazole (5.0 g) and N-(4-bromobutyl)phthalimide (17.2 g) were dissolved in dimethylformamide (250 ml), triethylamine (25.5 ml) was added to the solution, and the resulting mixture was stirred at 120° C. for 3 hours. The reaction mixture was left to cool to room temperature, then ethyl acetate and distilled water were added to the reaction mixture, and the layers were separated. The organic layer was washed with distilled water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in ethyl acetate. The reaction mixture was stirred, the deposited solid was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1). A mixed solution of ethyl acetate and hexane was added to the resulting roughly purified product, and the resulting mixture was stirred with heating to dissolve the roughly purified product, and then gradually cooled to room temperature to deposit a solid. The deposited solid was collected by filtration to obtain a phthalimide compound (324 mg). (2) By using the compound obtained in (1) mentioned above (324 mg) as a starting material, the title compound (183 mg) was obtained in the same manner as that of Reference Example 9, (2).

1. waitThe reaction mixture was left
2. temperatureto cool to room temperature
3. distillationethyl acetate and distilled water
4. additionwere added to the reaction mixture
5. customthe layers were separated
6. washThe organic layer was washed with distilled water
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. dissolutionthe resulting residue was dissolved in ethyl acetate
11. stirringThe reaction mixture was stirred
12. customthe deposited solid was removed by filtration
13. concentrationthe resulting filtrate was concentrated under reduced pressure
14. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1)
15. additionA mixed solution of ethyl acetate and hexane was added to the resulting roughly purified product
16. stirringthe resulting mixture was stirred
17. temperaturewith heating
18. dissolutionto dissolve the roughly purified product
19. temperaturegradually cooled to room temperature
20. filtrationThe deposited solid was collected by filtration

ORD record

ord-d24a80ee18ee4bfa96ea601efcf12d89

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139609B2