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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2412187Generated: November 2, 2026

Dimethylformamide → (2,4-Bis-benzyloxy-5-isopropyl-phenyl)-[5-(2-dimethylamino-ethoxy)-1,3-dihydro-isoindol-2-yl]-methanone

https://huagongshe.com/reaction/2412187

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
Reactant(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-hydroxy-1,3-dihydro-isoindol-2-yl)-methanoneHCID 66672264—
Product(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-[5-(2-dimethylamino-ethoxy)-1,3-dihydro-isoindol-2-yl]-methanoneHCID 59263095—

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of (2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone (100 mg, 0.2 mmol), 2-dimethylaminoethylchloride. HCl (72 mg, 0.5 mol) and K2CO3 (173 mg, 1.25 mmol) in DMF (5 ml) was heated at 90° C. for 16 hours. Dilute reaction mixture with EtOAc and filtered. The reaction mixture was diluted with EtOAc and filtered. The filtrate was reduced in vacuo and purified by flash column chromatography, eluting 100% DCM then 90% DMAW 90 to give the title compound as an off white gel (79 mg). MS: [M+H]+ 565

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08816087B2
Source datasetuspto-grants-2014_08
ORD IDord-794d7d216d234369bd497e85e1dbcaaa
Source noteuspto-grants-2014_08