Morpholine → 4-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluoromethylphenyl]morpholine

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	1-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene	HCID 58085697	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluoromethylphenyl]morpholine	HCID 58085699	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

1-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene (O3.004; 700 mg) was initially charged in dioxane (7 ml) and admixed successively with Pd(II) acetate (46 mg), cesium carbonate (2 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (118 mg) and morpholine (0.27 ml). Thereafter, the reaction mixture was heated to 90° C. for 7 h and then left to stand overnight. Subsequently, it was filtered and the filtrate was concentrated by rotary evaporation. The residue was purified using silica gel (50 g cartridge, n-heptane/EA gradient). 433 mg of the title compound were obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08076336B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-0933cabd1f6b449b922215fcb3060a8e
Source note	uspto-grants-2011_12