Reaktion #2375064

Reaktionsgleichung

HCl

NaH

6-(Dipropylamino)-3,5,6,7-tetrahydrocyclopent[f]isoindol-1(2H)-one

alpha-bromo-p-tolunitrile

→

133

4-[[6-(Dipropylamino)-3,5,6,7-tetrahydro-1-oxocyclopent[f]isoindol-2 (1H)-yl]methyl]benzonitrile

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with H2O
2. 2
   Extraktionextracted with CH2Cl2
3. 3
   WaschenThe organic layers were washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated on hi-vac
6. 6
   SonstigeThe reside was purified on silica gel
7. 7
   Wascheneluting with CH2Cl2 /MeOH
8. 8
   Sonstigeto give an oil that
9. 9
   Sonstigerecrystallized

Vorschrift

To a slurry of washed NaH (0.05 g, 1.32 mmol) in DMF (5 mL) was added a slurry of 6-(Dipropylamino)-3,5,6,7-tetrahydrocyclopent[f]isoindol-1(2H)-one (94, 0.30 g, 1.10 mmol) in DMF (10 mL). The slurry was heated to 84° C. and after 40 min, was treated with a solution of alpha-bromo-p-tolunitrile (0.43 g, 2.20 mmol) in DMF (10 mL). After 24 h, the reaction was quenched with H2O and extracted with CH2Cl2. The organic layers were washed with brine, dried (MgSO4), and concentrated on hi-vac. The reside was purified on silica gel, eluting with CH2Cl2 /MeOH to give an oil that was converted to an HCl salt and recrystallized to afford 133 as a white solid (m.p. 141-145° C.).

Quelle