Reaktion #69690

Reaktionsgleichung

2-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione

4-(3-chloropropyl)morpholine

potassium carbonate

→

title compound

Ausbeute 68.0%

2-(2,4-Dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-isoindole-1,3-dione

Ausbeute 68.0%

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted twice with 1N hydrochloric acid
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give a yellow solid which
8. 8
   Sonstigewas recrystallised from methanol/petrol

Vorschrift

A mixture of 2-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione (313 mg, 1.00 mmol), 4-(3-chloropropyl)morpholine (160 mg, 1.11 mmol) and potassium carbonate (350 mg, 2.5 mmol) in DMF (5 mL) was heated at 60° C. for 18 hours. The mixture was diluted with ethyl acetate and extracted twice with 1N hydrochloric acid. The aqueous extracts were made basic with solid potassium carbonate and extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4) and concentrated to give a yellow solid which was recrystallised from methanol/petrol then ethyl acetate/chloroform/petrol to give the title compound (298 mg, 68%) as an off-white solid. 1H NMR (methanol-d4) 7.72 (1H, t), 7.41 (1H, d), 7.39 (1H, d), 7.02 (1H, d), 6.51 (1H, d), 6.43 (1H, dd), 4.72 (2H, s), 4.27 (2H, t), 3.81 (3H, s), 3.76 (3H, s), 3.68 (4H, t), 2.61 (2H, t), 2.50 (4H, m), 2.05 (2H, qn). MS: [M+H]+ 441.

Quelle