Reaction #69700

Reaction equation

(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

Solvents

EtOAc

DMF

Conditions

Workup

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

Procedure

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