Dimethylformamide → N,N-diethyl-2-[4-(2-fluoro-4-nitro-phenyl)piperazin-1-yl]-2-phenyl-acetamide

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Reaction Steps

A 500 mL, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer and charged with anhydrous DMF (100 mL), 1-(2-fluoro-4-nitro-phenyl)-piperazine (4.0 g, 17.8 mmol), anhydrous K2CO3 (4.9 g, 35.5 mmol) and 2-bromo-N,N-diethyl-2-phenyl-acetamide (6.2 g, 23.0 mmol). The pale yellow reaction mixture was stirred at ambient temperature for 4 h, following which the solvent was removed on the rotary evaporator to yield a yellow colored semi-solid. MTBE (250 mL) was added and the resulting suspension was stirred at ambient temperature for 0.5 h and then filtered. The filtrate was extracted with 1.5N HCl (1×200 mL, then 1×100 mL). The aqueous layers were pooled, cooled to ˜0° C. in an ice bath and then basified with 2N NaOH (to pH ca. 13). The basified reaction mixture was extracted with MTBE (4×125 mL). The organic layers were pooled, dried over anhydrous sodium sulfate, filtered and concentrated to yield a brown colored oil. The oil was purified by silica gel chromatography (solvent: EtOAc/Hexane) to yield the title compound as a reddish-brown oil.

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