Cesium carbonate → Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methylpiperazine	HCID 53167	—
Reactant	Methyl 4-bromo-2-methylbenzoate	HCID 22031226	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate	HCID 54298739	89%

Reaction Conditions

Temperature	100 °C

Reaction Steps

In a pressure vessel was added methyl 4-bromo-2-methylbenzoate (500 mg, 2.18 mmol), Dioxane (5.0 mL), Cs2CO3 (1.4 g, 4.36 mmol), and Xantphos (92.0 mg, 0.16 mmol). The mixture was stirred and nitrogen was bubbled into the reaction for 5 min before adding in Palladium(II) acetate (58 mg, 0.08 mmol), and commercially available N-methyl piperazine (0.26 mL, 2.62 mmol). The vessel was then sealed and heated to 100° C. overnight. The reaction was cooled and filtered through celite. The supernatant was then concentrated and column purified (5:95 EtOAc:Hexanes) to give methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate (480 mg, 89% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242129B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-627032fea15145fcb80507eed3c08447
Source note	uspto-grants-2012_08