Triethylamine → 5-(4-Methylpiperazin-1-yl)-2-nitroaniline

A solution of 5-fluoro-2-nitrobenzenamine (3.0 g, 18.1 mmol), triethylamine (5.0 mL, 36.3 mmol), and 1-methylpiperazine (2.0 mL, 18.1 mmol) in dioxane (25 mL) was heated at reflux for 18 hr. After cooling to room temperature, the mixture was concentrated under reduced pressure and the residue dissolved in DCM (100 mL). This solution was washed with saturated aqueous sodium bicarbonate followed by brine, then dried over magnesium sulfate and concentrated under reduced pressure to give 5-(4-methylpiperazin-1-yl)-2-nitrobenzenamine (3.25 g) as a dark brown solid. A solution of 5-(4-methylpiperazin-1-yl)-2-nitrobenzenamine (3.25 g; 13.7 mmol) in absolute ethanol (40 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.30 g; 2.7 mmol) at room temperature for 17 hr. The mixture was filtered through diatomaceous earth and concentrated under reduced pressure to give 4-(4-methylpiperazin-1-yl)benzene-1,2-diamine (2.36 g).

1. temperatureat reflux for 18 hr
2. concentrationthe mixture was concentrated under reduced pressure
3. dissolutionthe residue dissolved in DCM (100 mL)
4. washThis solution was washed with saturated aqueous sodium bicarbonate
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-fd4173b905b14e25892254f46f84eff4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129396B2