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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 69036Generated: October 29, 2026

Trifluoroacetic acid → 1-Methyl-6-[3-(piperidin-4-yl-pyridin-4-ylmethyl-amino)-propoxy]-1H-quinolin-2-one

https://huagongshe.com/reaction/69036

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant4-{[3-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-piperidine-1-carboxylic acid tert-butyl esterHCID 66961857—
SolventDichloromethaneHCID 6344—
Product1-Methyl-6-[3-(piperidin-4-yl-pyridin-4-ylmethyl-amino)-propoxy]-1H-quinolin-2-oneHCID 6696070387.5%

Reaction Steps

Trifluoroacetic acid (30 ml) was added to a dichloromethane solution (10 ml) of 4-{[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester (1.08 g), and the mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. PL-HCO3 (40 g) was added to the dichloromethane solution of the residue and followed by celite filtration. The filtrate was condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=4:1). The purified product was condensed under reduced pressure to give the title compound (758 mg) as an orange oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822453B2
Source datasetuspto-grants-2014_09
ORD IDord-5b147059042d4e95823854064fe10ee3
Source noteuspto-grants-2014_09