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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348611Generated: October 31, 2026

Hydrochloric Acid → 2-{4-[(4-Dipropylaminobutyl amino)-methyl]benzyl}isoindole-1,3-dione

https://huagongshe.com/reaction/348611

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSulfuric acid magnesium salt (1:1)HCID 24083—
ReactantN,N-dipropylbutane-1,4-diamineHCID 7138396—
Reactant4-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)benzaldehydeHCID 23155547—
SolventMethanolHCID 887—
SolventTriethylamineHCID 8471—
Product2-{4-[(4-Dipropylaminobutyl amino)-methyl]benzyl}isoindole-1,3-dioneHCID 23155430—

Reaction Steps

The compound (103 mg) obtained in Example 25-1 was dissolved in anhydrous methanol (10 ml) and then added with the hydrochloride (114 mg) of the compound obtained in Example 1-2. Then, the solution was added with triethylamine (0.108 ml) and anhydrous magnesium sulfate (3 g), followed by stirring at room temperature for 1 hour. Anhydrous magnesium sulfate was removed from the solution by Celite filtration. Then, methanol was distilled off and the residue was dried using a vacuum pump. The residue was dissolved in anhydrous methanol (10 ml) and sodium borohydride (22.0 mg) was then gradually added under ice-cooling. The solution was warmed to room temperature and then stirred for 1 hour. After completion of the reaction, methanol was distilled off and the residue was then added with water and chloroform to extract the organic layer. After the organic layer had been dried with anhydrous sodium sulfate, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (60.3 mg) as a pale-yellow viscous liquid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07176227B2
Source datasetuspto-grants-2007_02
ORD IDord-941461c9ff524df891ba4fbe52b042d4
Source noteuspto-grants-2007_02