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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 553877Generated: October 31, 2026

Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

https://huagongshe.com/reaction/553877

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant3-Butenoic acidHCID 32743—
ReactantDiethyl cyanophosphonateHCID 76257—
Reactant(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidineHCID 69069541—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
SolventEthyl AcetateHCID 8857—
Product1-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-oneHCID 69074862—

Reaction Steps

Diethyl cyanophosphonate (0.67 mL) was added to a solution of (2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine (320 mg), vinylacetic acid (0.37 mL), and triethylamine (1.23 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for nine hours. Ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 100 mg of the title compound. The property value of the compound is as follows.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08048878B2
Source datasetuspto-grants-2011_11
ORD IDord-d40836c90a1e41a0b06b1275bc50066d
Source noteuspto-grants-2011_11