4-Hydroxybenzaldehyde → HCID 66910005, 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. This mixture 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 on 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., then stirred at room temperature for 16 h, and 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. 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-(4-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-(4-imidazole-1-ylmethyl-phenoxy)-butyl]-4-(2-methoxy-phenyl)-piperazine hydrochloride.

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 on 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. stirringstirred at room temperature for 16 h
21. customto terminate
22. customthe reaction
23. extractionThe organic layer was extracted 3 times with dichloromethane
24. customdried
25. concentrationconcentrated in vacuo
26. customThe residue was purified by column chromatography
27. dissolutionThis was dissolved in acetonitrile (30 ml)
28. temperaturethe reaction mixture was refluxed for 12 h
29. concentrationThis solution was then concentrated in a rotary evaporator
30. additiondiluted with methylene chloride
31. washwashed with brine
32. customthe resulting organic layer was dried
33. custompurified by column chromatography
34. dissolutionThe resulting 1-[4-(4-imidazole-1-ylmethyl-phenoxy)-butyl]-4-(2-methoxy-phenyl)-piperazine was dissolved in dichloromethane
35. additionthe solution was treated with a solution of HCl in ethyl ether
36. filtrationThe resulting precipitate was filtered

ORD record

ord-6e0c5eead92145e8b0403e85b751a3ae

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985752B2