1-Phenylpiperazine → HCID 67281887, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence