3-Hydroxybenzaldehyde → HCID 44538142, compound

Temperature

25 °C

A mixture of 3-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 in a rotary evaporator and diluted with ethyl acetate, 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 was 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 CHCl3 (30 ml) and was added with pyridine and thionyl chloride (5 mmol) at 0° C., and then the resulting reaction mixture was stirred at room temperature for 16 h, and water was added to terminate the reaction. The organic layer was extracted 3 times with dichloromethane, then dried and concentrated in vacuo, and the residue was purified by column chromatography. This was dissolved in acetonitrile (30 ml) and was added with imidazole (6 mmol), potassium 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. The resulting 1-[4-(3-imidazole-1-ylmethyl-phenoxy)-butyl]-4-(2-methoxy-phenyl)-piperazine was dissolved in dichloromethane and the solution was treated with a solution of HCl in ethyl ether. The resulting precipitate was filtered to give 1-[4-(3-imidazol-1-ylmethyl-phenoxy)-butyl]-4-(2-methoxy-phenyl)-piperazine hydrochloride.

1. concentrationThis solution was then concentrated in a rotary evaporator
2. additiondiluted with ethyl acetate
3. washwashed 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 CHCl3 (30 ml)
20. customthe resulting reaction mixture
21. stirringwas stirred at room temperature for 16 h
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
28. dissolutionThis was dissolved in acetonitrile (30 ml)
29. temperaturethe reaction mixture was refluxed for 12 h
30. concentrationThis solution was then concentrated in a rotary evaporator
31. additiondiluted with methylene chloride
32. washwashed with brine
33. customthe resulting organic layer was dried
34. custompurified by column chromatography
35. dissolutionThe resulting 1-[4-(3-imidazole-1-ylmethyl-phenoxy)-butyl]-4-(2-methoxy-phenyl)-piperazine was dissolved in dichloromethane
36. additionthe solution was treated with a solution of HCl in ethyl ether
37. filtrationThe resulting precipitate was filtered

ORD record

ord-016e8cf5f7f0430b83666288f2fe1508

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772299B2