Piperazine → N-(1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine

Participants

Reaction Steps

A solution of 1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethanamine (50.0 mg, 0.25 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (49.0 mg, 0.25 mmol) and diisopropylethylamine (129.0 mg, 4.0 mmol) in N,N-dimethylformamide (1 mL) was stirred at 110° C. for 16 h. The reaction was cooled to room temperature, poured over water and extracted with diethyl ether. The crude extract which contained mainly N-(1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine was used for the following reactions without further purification. A solution of N-(1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine (93.0 mg, 0.25 mmol), piperazine (432.0 mg, 5.0 mmol) and N,N-diisopropylethylamine (0.44 mL, 2.5 mmol) in acetonitrile (1 mL) was stirred at 80° C. for 16 h. The reaction mixture was cooled down and concentrated under reduced pressure. The residue was taken up in dichloromethane, washed with water, dried and concentrated in vacuo. The crude product was purified by silica chromatography (10% methanol in dichloromethane) to yield 15 mg (14%) of desired product. 1H NMR (400 MHz, CDCl3): δ 7.56 (d, 1H), 6.80 (d, 1H), 6.72 (s, 1H), 6.51 (d, 1H), 6.26 (dd, 1H), 5.99 (dd, 2H), 5.92 (s, 1H), 4.59 (m, 1H), 3.21 (m, 4H), 2.57 (m, 4H), 1.59 (d, 3H); MS (ESI) m/z: 438.3 (M++1).

Provenance & Evidence