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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 56212Generated: October 27, 2026

But-1-ene-1,3-dione → N-(4-((2-(-adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-oxobutanamide

https://huagongshe.com/reaction/56212

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBut-1-ene-1,3-dioneHCID 12642904—
ReactantN1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamineHCID 131736912—
SolventEthyl AcetateHCID 8857—
ProductN-(4-((2-(-adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-oxobutanamideHCID 9002256064.5%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of N1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamine (0.38 g, 1.32 mmol) in EtOAc (20 mL) was added acetyl ketene (0.22 g, 2.62 mmol) and the mixture was stirred at 90° C. overnight. The mixture was then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a white solid (317 mg, 64%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434695B2
Source datasetuspto-grants-2016_09
ORD IDord-52580cd14e2a41c1a385092a05fc4b4f
Source noteuspto-grants-2016_09