Cesium carbonate → Methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	N,N-Dimethylethylenediamine	HCID 66053	—
Reactant	Methyl 4-iodobenzoate	HCID 69273	—
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	Methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate	HCID 57440398	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

Methyl 4-iodobenzoate (1 g, 3.82 mmol), XANTPHOS (0.033 g, 0.057 mmol), Pd2(dba)3 (0.035 g, 0.038 mmol), Cs2CO3 (1.741 g, 5.34 mmol) was added to a sealed tube with septa and purged with argon 3×. N,N-dimethyl-1,2-ethanediamine (0.404 g, 4.58 mmol) and 1,4-Dioxane (4 mL) was then added and was stirred at 110° C. for Overnight. The reaction mixture was cooled to room temp and diluted with ethyl acetate and filtered through celite. The organic solvent was concentrated. The product was used without further purification. MS: cal'd 223 (MH+), exp 223 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08119685B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-b6bee657ad944f6c96dbf5fbaaa25d63
Source note	uspto-grants-2012_02