Morpholine → Methyl 2-methoxy-5-(morpholin-4-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Methyl 5-iodo-2-methoxybenzoate	HCID 11011762	—
Catalyst	HCID 66545394	HCID 66545394	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 2-methoxy-5-(morpholin-4-yl)benzoate	HCID 67105971	39.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

5-Iodo-2-methoxy-benzoic acid methyl ester (500 mg, 1.7 mmol), morpholine (223 μl, 2.5 mmol), cesium carbonate (850 mg, 2.7 mmol), xantphos (60 mg, 0.1 mmol) and bis(dibenzylideneacetone)dipalladium (35 mg, 0.04 mmol) were suspended in dioxane (5 ml) and heated at 100° C. for 5 h. The mixture was then cooled, filtered and the residue was purified by flash column chromatography [SiO2, EtOAc] to give 2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester (170 mg) as a colourless solid. (LC/MS (basic method): Rt 2.35 min, [M+H]+ 252).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07977477B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-003f43ee83234cdab93966f3b4729609
Source note	uspto-grants-2011_07