Réaction #69700

Équation de réaction

(2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone

2-dimethylaminoethylchloride

HCl

K2CO3

→

title compound

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

Solvants

EtOAc

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONDilute
2. 2
   Filtrationfiltered
3. 3
   workup.ADDITIONThe reaction mixture was diluted with EtOAc
4. 4
   Filtrationfiltered
5. 5
   Autrepurified by flash column chromatography
6. 6
   Lavageeluting 100% DCM

Mode opératoire

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 mmol) 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

Source