N,N'-Dimethylethylenediamine → 4-(4-Aminophenyl)morpholin-3-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	4-Iodoaniline	HCID 10893	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Morpholinone	HCID 66953	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(4-Aminophenyl)morpholin-3-one	HCID 11194854	50.3%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a blue solution of 3-morpholinone (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N′-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110° C. overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612089B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-f2efe79bd0984025a07da9ca23bd5d4d
Source note	uspto-grants-2009_11