1-(2-Methoxyphenyl)piperazine → HCID 178489561, 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-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. 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. This product was dissolved in THF (50 ml) and trace water and was added with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (10 mmol). The reaction mixture was stirred at 52° C. After 3 h, the solvent was removed and the residue was treated with 5% NaHCO3, then the organic layer was extracted 3 times with ethylacetate, then dried and concentrated in vacuo, and 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. dissolutionThis product was dissolved in THF (50 ml)
20. stirringThe reaction mixture was stirred at 52° C
21. waitAfter 3 h
22. customthe solvent was removed
23. additionthe residue was treated with 5% NaHCO3
24. extractionthe organic layer was extracted 3 times with ethylacetate
25. customdried
26. concentrationconcentrated in vacuo
27. customthe residue was purified by column chromatography

ORD record

ord-aeb5369f4ffa438990529ca57705bf0e

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964605B2