Reaktion #2053623

Reaktionsgleichung

4-bromo-2-fluoro-1-nitrobenzene

dimethylamine ethanol

5-bromo-N,N-dimethyl-2-nitrobenzenamine

benzoyl piperazine

BINAP

cesium carbonate

→

(4-(3-(dimethylamino)-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone

Ausbeute 21.2%

Lösungsmittel

ethyl acetate

—

hexanes

NMP

NMP

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solids (1.03 g, 90%) were filtered
2. 2
   Sonstigedried under high vacuum

Vorschrift

A solution of 4-bromo-2-fluoro-1-nitrobenzene (1.0 g, 4.5 mmol) and 2.0 M dimethylamine ethanol solution (6.9 ml, 13.6 mmol) in 20 ml NMP was stirred at room temperature for 16 hours. The solution was added 200 ml water. The solids (1.03 g, 90%) were filtered dried under high vacuum. A solution of 5-bromo-N,N-dimethyl-2-nitrobenzenamine (0.2 g, 0.8 mmol), benzoyl piperazine (0.19 g, 1.0 mml), Tris(dibenzylideneacetone)dipalladium (9 mg), BINAP (38 mg) and cesium carbonate (0.24 g, 1.2 mmol) in 20 ml NMP was stirred at 100° C. under argon atmosphere for 16 hours. The reaction was cooled to room temperature before filtration. (4-(3-(dimethylamino)-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone (0.06 g, 20%) was obtained after flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.93 (s, 6H), 3.40-3.57 (m, 8H), 6.26 (d, J=2.6 Hz, 1H), 6.35 (dd, J=2.6, 9.6 Hz, 1H), 7.48 (m, 5H), 7.98 (d, J=9.6 Hz, 1H).

Quelle