Potassium Iodide → HCID 44538851, compound

A mixture of 4-cyanophenol (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. This mixture was then washed with brine, and the resulting organic layer was dried and purified by column chromatography. This product was dissolved in isopropanol (50 ml) and was added with 1-(2-chloro-phenyl)-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, this mixture was then washed with brine, and the resulting organic layer was dried and purified by column chromatography. This was dissolved in dried THF (50 ml) and was added with LAH (5 mmol) at 0° C., the reaction mixture was stirred at room temperature for 6 h, and H2O:1N NaOH:H2O (1:1:3) was added to terminate the reaction at 0° C. This crude product was dried with MgSO4 and concentrated in vacuo, and the residue was purified by column chromatography. The product was added to ethylchloroformate (5 mmol) and triethylamine (6 mmol), at 0° C. and was stirred for 2 hr in 20 ml of dichloromethane. This solution was diluted with dichloromethane and washed with water, and the resulting organic layer was dried and concentrated in vacuo. This was dissolved in dried THF and was added with LAH (5 mmol) at 0° C. The reaction mixture was stirred at room temperature for 6 h, and H2O:1N NaOH:H2O (1:1:3) was added to terminate the reaction at 0° C. This crude product was dried with MgSO4 and concentrated in vacuo. This product was dissolved in THF (20 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, then dried and concentrated in vacuo. The residue was purified by column chromatography.

1. concentrationThis solution was then concentrated in 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 product was dissolved in isopropanol (50 ml)
7. temperaturethe reaction mixture was refluxed for 12 h
8. concentrationThis solution was then concentrated in a rotary evaporator
9. additiondiluted with methylene chloride
10. washthis mixture was then washed with brine
11. customthe resulting organic layer was dried
12. custompurified by column chromatography
13. dissolutionThis was dissolved in dried THF (50 ml)
14. customto terminate
15. customthe reaction at 0° C
16. dry with materialThis crude product was dried with MgSO4
17. concentrationconcentrated in vacuo
18. customthe residue was purified by column chromatography
19. washwashed with water
20. customthe resulting organic layer was dried
21. concentrationconcentrated in vacuo
22. dissolutionThis was dissolved in dried THF
23. stirringThe reaction mixture was stirred at room temperature for 6 h
24. customto terminate
25. customthe reaction at 0° C
26. dry with materialThis crude product was dried with MgSO4
27. concentrationconcentrated in vacuo
28. dissolutionThis product was dissolved in THF (20 ml)
29. stirringThe reaction mixture was stirred at room temperature for 4 h
30. stirringAfter 5 h stirring at room temperature
31. customto terminate
32. customthe reaction
33. extractionThe organic layer was extracted 3 times with dichloromethane
34. customdried
35. concentrationconcentrated in vacuo
36. customThe residue was purified by column chromatography

ORD record

ord-55d5fd4e191b42b7a3b528f0e3af9c11

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964605B2