Ethanol → HCID 67281639, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence