Felbinac → N-methoxy-N-methyl-4-biphenylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Felbinac	HCID 3332	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	HCID 178418300	HCID 178418300	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-methoxy-N-methyl-4-biphenylacetamide	HCID 17815837	83.3%

Reaction Steps

A mixture of 2-(biphenyl-4-yl)acetic acid (1 g, 4.7 mmol), N,O-dimethylhydroxylamine hydrochloride (458 mg, 4.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (900 g, 4.7 mmol), hydroxybenzotriazole (635 mg, 4.7 mmol), and triethylamine (1.42 g, 14.1 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. When TLC indicated that 2-(biphenyl-4-yl)acetic acid was consumed, the reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=8:1) to afford 2-(biphenyl-4-yl)-N-methoxy-N-methylacetamide (1.0 g, yield 83%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09283229B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-e396328a60ad4d90a4e19fc9fe2e92b4
Source note	uspto-grants-2016_03