Reaction #69738

Reaction equation

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

4-(3-chloropropyl)morpholine

caesium carbonate

→

(2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone

Yield 71.5%

Solvents

DMF

Conditions

Workup

1. 1
   Otherthen evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Washwashed with brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Otherevaporated
6. 6
   OtherPurification of the crude material
7. 7
   Washelution
8. 8
   Otherform 0% to 10% MeOH/EtOAc

Procedure

A mixture of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(4-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone (2 g; 4.07 mmol), 4-(3-chloropropyl)morpholine (1.66 g; 2.5 equiv.) and caesium carbonate (8.3 g; 6.25 equiv) in DMF was heated at 90° C. overnight then evaporated. The residue was dissolved in EtOAc, washed with brine, dried (MgSO4) and evaporated. Purification of the crude material using a Biotage SP4 (40 S, 40 ml/min), using gradient elution form 0% to 10% MeOH/EtOAc gave 1.8 g of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone as a pale yellow gum. MS: [M+H]+ 619.

Source