(3RS)-N-Methyl-3-phenyl-3-[2-(trifluoroMethyl)-phenoxy]propan-1-aMine Hydrochloride(2-TrifluoroMethylisoMer of Fluoxetine Hydro-chloride)

Description

N-Formylfluoxetine is impuritie generated during the production of fluoxetine. Fluoxetine (Fluoxetine, trade name Prozac) is a drug developed by Eli Lilly and launched in 1987 for the treatment of depression. It can also be used to treat symptoms of alcoholism, headaches, migraines, anxiety, and obesity.

Uses

N-Formylfluoxetine is an impurity generated during the production process of fluoxetine, which can be used as a reference substance for pharmaceutical impurities.

Synthesis

Fluoxetine (154.7 mg, 0.5 mmol), and a stirrer were placed into the reaction tube, and after displacing the inert gas, DMF (193 L, 2.5 mmol) was added and the reaction tube was sealed. The reaction tube was placed in an oil bath reactor at 150 C for 96 h with stirring. After cooling to room temperature, diluted with 15mL water, and extracted with ethyl acetate for 3 times, 15mL each time, combined the extracts, and dried with anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and then the crude product was obtained as pure product by column chromatography with the eluent of ethyl acetate: petroleum ether = 1:2 (containing 1% triethylamine). Yellow oily liquid, yield 76%.