4-Hydroxybenzaldehyde → HCID 44538652, compound

Temperature

25 °C

A mixture of 4-hydroxybenzaldehyde (5 mmol), 1-bromo-4-chlorobutane (5 mmol), and potassium carbonate (15 mmol) was refluxed in 100 ml of acetone for 6 h. This solution was then concentrated on a rotary evaporator and diluted with ethyl acetate. This mixture was then washed with brine, and the resulting organic layer was dried and purified by column chromatography. This was dissolved in methanol (50 ml) and was added with sodium borohydride (10 mmol) at 25° C., and stirred at 25° C. for 2 h. This solution was then concentrated in a rotary evaporator and diluted with methylene chloride, then washed with brine, and the resulting organic layer was dried and concentrated in vacuo. The crude product was dissolved in isopropanol (50 ml) and was added with 1-(2-methoxyphenyl)-piperazine (5 mmol), sodium carbonate (15 mmol), and potassium iodide (5 mmol) at 25° C., and the reaction mixture was refluxed for 12 h. This solution was then concentrated in a rotary evaporator and diluted with methylene chloride, then washed with brine, and the resulting organic layer was dried and purified by column chromatography. This product was dissolved in THF (50 ml) and was added with 1,1′-carbonyl diimidazole (12 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 h, followed by the addition of excess ammonium hydroxide (10 ml) at 0° C. After 5 h stirring at room temperature, water was added to terminate the reaction. The organic layer was extracted 3 times with dichloromethane, dried, and concentrated in vacuo. The residue was purified by column chromatography.

1. concentrationThis solution was then concentrated on a rotary evaporator
2. additiondiluted with ethyl acetate
3. washThis mixture was then washed with brine
4. customthe resulting organic layer was dried
5. custompurified by column chromatography
6. dissolutionThis was dissolved in methanol (50 ml)
7. concentrationThis solution was then concentrated in a rotary evaporator
8. additiondiluted with methylene chloride
9. washwashed with brine
10. customthe resulting organic layer was dried
11. concentrationconcentrated in vacuo
12. dissolutionThe crude product was dissolved in isopropanol (50 ml)
13. temperaturethe reaction mixture was refluxed for 12 h
14. concentrationThis solution was then concentrated in a rotary evaporator
15. additiondiluted with methylene chloride
16. washwashed with brine
17. customthe resulting organic layer was dried
18. custompurified by column chromatography
19. dissolutionThis product was dissolved in THF (50 ml)
20. stirringThe reaction mixture was stirred at room temperature for 4 h
21. stirringAfter 5 h stirring at room temperature
22. customto terminate
23. customthe reaction
24. extractionThe organic layer was extracted 3 times with dichloromethane
25. customdried
26. concentrationconcentrated in vacuo
27. customThe residue was purified by column chromatography

ORD record

ord-272d484c790741929019fac7061c6600

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964605B2