Cesium carbonate → 1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Isopropylpiperazine	HCID 78013	—
Reactant	5-Chloro-2-nitroanisole	HCID 81110	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine	HCID 58748443	90%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To 4-chloro-2-(methyloxy)-1-nitrobenzene (3.0 g, 16.0 mmol) in dioxane (75 mL) was added 1-(1-methylethyl)piperazine (4.1 g, 32.0 mmol), XANTPHOS (1.4 g, 2.4 mmol), and Cs2CO3 (10.4 g, 32.0 mmol). The mixture was bubbled with N2 for 15 min prior to the addition of Pd2(dba)3 (1.5 g, 1.6 mmol). The reaction was stirred at 100° C. for 5 h. Following cooling to room temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and water (100 mL). The organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by silica gel chromatography to afford 1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine (4.0 g, 90% yield). ESIMS (M+H)+=280.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07981903B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-1a7873c376894e9c99832db47f3410f8
Source note	uspto-grants-2011_07