Reaction #145

Reaction equation

COc1ccc(Br)cc1[N+](=

CC(=O)N1CCNCC1

→

COc1ccc(N2CCN(C(C)=O

Yield 1.4%

Solvents

C1COCCO1

Conditions

Procedure

4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol) was added in one portion to 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) in dioxane (20 ml) under nitrogen. The resulting mixture was stirred at 120 °C for 3 hours. The reaction mixture was filtered through celite and the fitrate evaporated to dryness. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (0.025 g, 1.385 %) as a brown oil.

Source