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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 502399Generated: October 25, 2026

Trifluoroacetic acid → 2-{4-[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

https://huagongshe.com/reaction/502399

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantDiisopropylethylamineHCID 81531—
Reactant3-Ethoxy-4-methoxybenzaldehydeHCID 244728—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant4-[4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterHCID 68454766—
Reactant2-Methyl-2-[4-(piperidin-4-ylcarbamoyl)-phenyl]-propionic acid methyl esterHCID 68459381—
SolventAcetic AcidHCID 176—
SolventEthanolHCID 702—
SolventDichloromethaneHCID 6344—
Product2-{4-[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl esterHCID 68456987—

Reaction Steps

In analogy to the procedure described in example 50k), 2-methyl-2-[4-(piperidin-4-ylcarbamoyl)-phenyl]-propionic acid methyl ester [prepared from 4-[4-(1-methoxycarbonyl-1-methyl-ethyl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester by treatment with TFA in dichloromethane in analogy to the preparation described in example 50i)] was reacted with 3-ethoxy-4-methoxybenzaldehyde, sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless foam. MS: 469.3 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07772253B2
Source datasetuspto-grants-2010_08
ORD IDord-fdc10a0d6ea4495eb4809cc32cf05a58
Source noteuspto-grants-2010_08