1-Phenylpiperazine → HCID 67281887, compound

Temperature

80 °C

3-chloropropiophenone (14.77 mmol) and phenylpiperazine (17.7 mmol) were dissolved in acetonitrile (50 mL), and triethylamine (17.7 mmol) was added thereto, and the resulting mixture was stirred at 80° C. for 24 hours. The resulting reaction mixture was diluted with water, and extracted several times with ethyl acetate. The extracted organic phase was collected, washed with water and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under a reduced pressure to obtain a pellet. The prepared pellet (1.75 mmol) was dissolved in tetrahydrofuran (20 mL), and 1.5 mole of a cyclohexanelithium diimide (1.92 mmol) solution was added dropwise while the resulting mixture was maintained to a temperature of −78° C. Then, the resulting mixture was stirred at −78° C. for 10 minutes, and then stirred at 0° C. for 30 minutes. After the resulting mixture was cooled again and maintained to a temperature of −78° C., N-fluorobenzenesulfonimide (2.27 mmol) was added to the mixture, and the resulting mixture was stirred at a room temperature for 2 hours. The resulting reaction mixture was diluted by adding a saturated ammonium chloride solution, and the diluted reaction mixture was extracted several times with ethylacetate. The resulting organic phase was dried over magnesium sulfate, and concentrated under a reduced pressure. In this case, the resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:4) to obtain a crude compound. The prepared crude compound (1.5 mmol) was dissolved in methanol (20 mL), and NaBH4 (3.0 mmol) was added slowly to the mixture. The resulting mixture was stirred at a room temperature for 1 hour, and concentrated under a reduced pressure to remove off solvents. The resulting pellet was then purified with column chromatography (hexane:ethylacetate=1:2) to obtain a crude compound. The prepared crude compound (1 mmol) was dissolved in tetrahydrofuran (20 mL), and 1,1′-carbodiimidazole (2 mmol) was added thereto, and the resulting mixture was stirred at a room temperature for 2 hour. Then, excessive ammonium hydroxide was added to the mixture, and the resulting mixture was stirred at a room temperature for additional 2 hours. The resulting reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, and then concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:4) to obtain a final compound.

1. customThe resulting reaction mixture
2. extractionextracted several times with ethyl acetate
3. customThe extracted organic phase was collected
4. washwashed with water
5. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
6. concentrationconcentrated under a reduced pressure
7. customto obtain a pellet
8. temperaturewas maintained to a temperature of −78° C
9. stirringThen, the resulting mixture was stirred at −78° C. for 10 minutes
10. stirringstirred at 0° C. for 30 minutes
11. temperatureAfter the resulting mixture was cooled again
12. additionwas added to the mixture
13. stirringthe resulting mixture was stirred at a room temperature for 2 hours
14. customThe resulting reaction mixture
15. additionwas diluted
16. customthe diluted reaction mixture
17. extractionwas extracted several times with ethylacetate
18. dry with materialThe resulting organic phase was dried over magnesium sulfate
19. concentrationconcentrated under a reduced pressure
20. customIn this case, the resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:4)
21. customto obtain a crude compound
22. stirringThe resulting mixture was stirred at a room temperature for 1 hour
23. concentrationconcentrated under a reduced pressure
24. customto remove off solvents
25. customThe resulting pellet was then purified with column chromatography (hexane:ethylacetate=1:2)
26. customto obtain a crude compound
27. stirringthe resulting mixture was stirred at a room temperature for 2 hour
28. stirringthe resulting mixture was stirred at a room temperature for additional 2 hours
29. customThe resulting reaction mixture
30. extractionextracted several times with ethyl acetate
31. customto obtain an organic phase
32. dry with materialThe prepared organic phase was dried over magnesium sulfate
33. concentrationconcentrated under a reduced pressure
34. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:4)

ORD record

ord-ba864f826a88448e9b15ba05ce79669c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815852B2