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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60581Generated: October 26, 2026

1,2-Dimethoxyethane → (4-Benzyl-4-hydroxypiperidin-1-yl)(5-(pyridin-4-yl)-1,3-benzodioxol-4-yl)methanone

https://huagongshe.com/reaction/60581

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
Reactant(Pyridin-4-yl)boronic acidHCID 2734379—
Reactant(4-Benzyl-4-hydroxypiperidin-1-yl)(5-bromo-1,3-benzodioxol-4-yl)methanoneHCID 86680850—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Product(4-Benzyl-4-hydroxypiperidin-1-yl)(5-(pyridin-4-yl)-1,3-benzodioxol-4-yl)methanoneHCID 86680851170.7%

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of (4-benzyl-4-hydroxypiperidin-1-yl) (5-bromo-1,3-benzodioxol-4-yl)methanone (0.50 g), pyridine-4-boronic acid (0.22 g), sodium carbonate (0.38 g), tetrakis(triphenylphosphine)palladium(0) (0.069 g), water (0.50 mL) and DME (2.5 mL) was stirred at 150° C. for 1 hr under microwave irradiation. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (0.85 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440990B2
Source datasetuspto-grants-2016_09
ORD IDord-4c24d83293bb4de397e1430573d9cf87
Source noteuspto-grants-2016_09