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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 564162Generated: October 29, 2026

Trifluoroacetic acid → 4-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-one

https://huagongshe.com/reaction/564162

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantSodium BicarbonateHCID 516892—
Reactant{4-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic Acid Tert-Butyl EsterHCID 67006987—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Product4-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-oneHCID 58042805—

Reaction Steps

To 100 mg (0.22 mmol) {4-[2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic acid tert-butyl ester (example 19.1a) in DCM is added at RT 0.70 mL trifluoro-acetic acid. The reaction mixture is stirred 2 h at RT, neutralized with aqueous saturated NaHCO3-solution and is diluted with water and DCM. The layers are separated, the aqueous phase is extracted twice with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067590B2
Source datasetuspto-grants-2011_11
ORD IDord-fe6e93aa3a3344ee81f01348629ece05
Source noteuspto-grants-2011_11