Ethanol → HCID 67281639, compound

Temperature

72 °C

Phenyl-1-propenyl-ketone (4.1 mmol) and 4-methoxy phenylpiperazine (4.9 mmol) were dissolved in ethanol (30 mL), and the resulting mixture was stirred at 72° C. for 48 hours. The mixture was distilled under a reduced pressure, diluted with water, and then extracted twice with ethyl acetate. The resulting organic phase was distilled under a reduced pressure, dried over magnesium sulfate, and filtered, and the resulting filtrate was concentrated under a reduced pressure, and purified with column chromatography (hexane:ethylacetate=4:1) to obtain a crude compound. The prepared crude compound (2.9 mmol) was dissolved in methanol (20 mL), and NaBH4 (3.8 mmol) was added slowly to the mixture. The resulting mixture was stirred at a room temperature for 2 hour, and concentrated under a reduced pressure, and obtained a yellow pellet. The prepared yellow pellet was purified with column chromatography (hexane:ethylacetate=1:1). The purified compound (2 mmol) was dissolved in tetrahydrofuran (15 mL), and 1,1′-carbodiimidazole (4 mmol) was added to the purified compound. The resulting mixture was stirred at a room temperature for 1 hour, and 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 concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a final compound.

1. distillationThe mixture was distilled under a reduced pressure
2. additiondiluted with water
3. extractionextracted twice with ethyl acetate
4. distillationThe resulting organic phase was distilled under a reduced pressure
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationthe resulting filtrate was concentrated under a reduced pressure
8. custompurified with column chromatography (hexane:ethylacetate=4:1)
9. customto obtain a crude compound
10. stirringThe resulting mixture was stirred at a room temperature for 2 hour
11. concentrationconcentrated under a reduced pressure
12. customobtained a yellow pellet
13. customThe prepared yellow pellet was purified with column chromatography (hexane:ethylacetate=1:1)
14. stirringThe resulting mixture was stirred at a room temperature for 1 hour
15. stirringthe resulting mixture was stirred at a room temperature for additional 2 hours
16. customThe resulting reaction mixture
17. extractionextracted several times with ethyl acetate
18. customto obtain an organic phase
19. dry with materialThe prepared organic phase was dried over magnesium sulfate
20. concentrationconcentrated under a reduced pressure
21. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-9fa5c15da79b438eb98e6abc45293df8

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815852B2