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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1433617Generated: October 25, 2026

Dimethylformamide → 4-(4-Amino-3-fluorophenoxy)-7-(1-methylpiperidin-3-ylmethoxy)quinoline-6-carbonitrile

https://huagongshe.com/reaction/1433617

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Chloromethyl-1-methylpiperidinium chlorideHCID 106690—
Reactant4-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinolineHCID 135829379—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product4-(4-Amino-3-fluorophenoxy)-7-(1-methylpiperidin-3-ylmethoxy)quinoline-6-carbonitrileHCID 2293677610.9%

Reaction Conditions

Temperature20 °C

Reaction Steps

After adding dimethylformamide (4 ml), 3-chloromethyl-1-methylpiperidine hydrochloride (621 mg) and potassium carbonate (840 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (400 mg), the mixture was stirred at 20° C. for 3 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (60 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07612092B2
Source datasetuspto-grants-2009_11
ORD IDord-22e0d2fb84ed4828a052e31fc8ddecab
Source noteuspto-grants-2009_11