Nitrogen → 1-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methylpiperazine	HCID 53167	—
Reactant	4-Bromo-2-nitroanisole	HCID 118533	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine	HCID 59441886	74%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To an N2 degassed solution of 1,4-dioxane (20 mL), was added 4-bromo-1-(methyloxy)-2-nitrobenzene (0.5 g, 2.16 mmol), XANTPHOS (0.37 g, 0.65 mmol, Aldrich), Pd2(dba)3(0.39 g, 0.43 mmol, Aldrich), Cs2CO3 (1.4 g, 4.3 mmol, Aldrich), and 1-methylpiperazine (0.43 g, 4.3 mmol, Aldrich). After heating overnight at 90° C., the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL), the organic layer adsorbed to silica gel and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to afford 1-methyl-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.4 g, 74%) as a tan solid. ESIMS (M+H)+=252.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07981903B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-ae041231a94b47ae9f511ff9e250adc5
Source note	uspto-grants-2011_07