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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2247510Generated: November 1, 2026

Ethanol → (E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

https://huagongshe.com/reaction/2247510

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantWaterHCID 962—
ReactantSodium HydroxideHCID 14798—
Reactant(E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl esterHCID 66961755—
SolventEthyl AcetateHCID 8857—
Product(E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-oneHCID 5917084572.8%

Reaction Steps

To an ethanol (2.0 mL) solution of (E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester (120 mg), 2N sodium hydroxide solution (1.0 mL) was added. After carrying out heat-refluxing of the reaction solution for 30 minutes and confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1), and 78.9 mg of the title compound was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07687640B2
Source datasetuspto-grants-2010_03
ORD IDord-04d2b74aca5941f69230132bd875647d
Source noteuspto-grants-2010_03