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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 404225Generated: October 26, 2026

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

https://huagongshe.com/reaction/404225

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 numberUS08748459B2
Source datasetuspto-grants-2014_06
ORD IDord-2c98c21681124c399a921f0306d71e88
Source noteuspto-grants-2014_06