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

https://huagongshe.com/reaction/419549

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 rt, the reaction mixture was diluted with EtOAc (150 mL) and H2O (100 mL). The organic layer was dried over NaSO4 taken to a residue under reduced pressure, and purified by silica gel chromatography to afford the title compound of step A (4.0 g, 90% yield). MS (ESI) (M+H)+=280.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093239B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-f2e98b83387343128741cb9ca1ef9ed5
Source note	uspto-grants-2012_01