2-(4-METHYLPIPERAZIN-1-YL)-5-NITROANILINE synthesis

Yield:5367-66-8 82%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 80; for 16 h;

Steps:

1

To a solution of 2-fluoro-5-nitroaniline (2.0g, 12mmol) in DMF (16.0mL), Cs₂C0₃ (8.3g, 25mmol) and N-methyl piperazine (1.53g, 15mmol) were added, and the resulting mixture was heated to 80°C for 16h. The reaction mixture was cooled to room temperature, diluted with water (50.0mL) and extracted with ethyl acetate (50.0mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduce pressure. The residue was purified by silica gel column chromatography to obtain 1 (2.3g, 82%) as a yellow solid. 1H NMR (400 MHz, DMSO-d₆): δ 2.22 (s, 3H), 2.49 (m, 4H), 2.9 (brs, 4H), 5.2 (s, 2H), 6.98 (d, J = 8.6 Hz, 1H), 7.41-7.44 (dd, J = 2.7, 8.6 Hz, 1H), 7.52 (d, J = 2.7 Hz, 1H). MS m/z (M+H): 237.1

References:

WO2014/149164,2014,A1 Location in patent:Paragraph 00868