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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1667332Generated: October 26, 2026

Triethylamine → 4-Fluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide dihydrochloride

https://huagongshe.com/reaction/1667332

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantSodium HydroxideHCID 14798—
Reactant4-Fluorobenzoyl chlorideHCID 67879—
Reactant(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanoneHCID 11401723—
SolventDichloromethaneHCID 6344—
Product4-Fluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide dihydrochlorideHCID 67441227—

Reaction Steps

Stir a mixture of 2-Amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.150 g), 4-fluorobenzoyl chloride (0.218 g), triethylamine (0.192 mL) and dichloromethane at room temperature for 4 hours. Add 1N aqueous NaOH to basify the reaction mixture. Extract the mixture with dichloromethane, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and purify the residue by HPLC to provide the free base of the title compound. Re-dissolve the free base in diethyl ether and add excess 1 M HCl. Evaporate the solvent and dry the residue under vacuum to obtain 80 mg of the title compound. M.p. 75-80° C.; HRMS: 342.1605 (obs.) (Cal. 342.1618).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08044207B2
Source datasetuspto-grants-2011_10
ORD IDord-5aa5bcb2cf9940bfa45cd5c7587572e8
Source noteuspto-grants-2011_10