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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2415363Generated: October 26, 2026

Water → 1-(3,4-Methylenedioxyphenyl)-2-(pyridin-4-yl)methyl-2,3,4,9-tetrahydro-1H-beta-carboline

https://huagongshe.com/reaction/2415363

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-(Chloromethyl)pyridinium chlorideHCID 74570—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 201172—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product1-(3,4-Methylenedioxyphenyl)-2-(pyridin-4-yl)methyl-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 22640314—

Reaction Steps

A solution of 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (2.92 g, 10 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24), 4-picolylchloride hydrochloride (1.64 g, 10 mmol) and DBU (3.1 g, 20 mmol) in DMF (50 mL) was stirred at room temperature for 16 h. Water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture. The solute, present in the organic phase, was purified by column chromatography (silica gel, ethyl acetate) to yield the product as an off-white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06818646B2
Source datasetuspto-grants-2004_11
ORD IDord-336a8f0a64494055b49450cc96fa8032
Source noteuspto-grants-2004_11