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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 387958Generated: October 25, 2026

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

https://huagongshe.com/reaction/387958

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 saline 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 numberUS08372981B2
Source datasetuspto-grants-2013_02
ORD IDord-f2152a86cd90490a9ea71f590a261188
Source noteuspto-grants-2013_02