(4-Aminophenoxy)benzene → (2,2-Dimethoxyethyl)-(4-phenoxyphenyl)amine

Participants

Role	Name	HCID	Charge
Reactant	(4-Aminophenoxy)benzene	HCID 8764	—
Reactant	2-Bromo-1,1-dimethoxyethane	HCID 81672	—
Reactant	2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine	HCID 3513851	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(2,2-Dimethoxyethyl)-(4-phenoxyphenyl)amine	HCID 21873313	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of 4-phenoxyaniline (915 mg) in dimethylformamide (5 ml) was mixed with bromoacetaldehyde dimethyl acetal (1.1 ml) and BEMP (1.9 ml). The reaction mixture was shaken at 100° C. for 16 hours. Volatiles were removed and the residue was purified by chromatography on silica gel (eluent: dichloromethane/hexane 1:2, later 1:1 with in each case 1% v/v 7N ammonia solution in methanol). The product with the molecular weight of 273.33 (C16H19NO3); MS (ESI): 274 ([M+H]+), was obtained in this way.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07141561B2
Source dataset	uspto-grants-2006_11
ORD ID	ord-1e2893f94d5746589681acb1a983916d
Source note	uspto-grants-2006_11