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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1749851Generated: November 4, 2026

Formaldehyde → 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one

https://huagongshe.com/reaction/1749851

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
Reactant6-Hydroxy-3-coumaranoneHCID 235717—
Reactantrel-(2R,6S)-2,6-dimethylpiperazineHCID 6950261—
SolventEthanolHCID 702—
Product7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-oneHCID 7127869731.3%

Reaction Steps

A solution of 6-hydroxybenzofuran-3(2H)-one (0.300 g, 2.00 mmol) in ethanol (2 mL) was added with cis-3,5-dimethylpiperazine (0.288 g, 2.00 mmol), and 37% aqueous formaldehyde (0.162 g, 2.00 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, and then concentrated. The resulting solid was dissolved in ethyl acetate, and the precipitated solid was removed by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one (0.173 g, 31%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09156827B2
Source datasetuspto-grants-2015_10
ORD IDord-4528504b84a640b5996ecf1f7b7a3f6b
Source noteuspto-grants-2015_10