反应详情

A stirred mixture of 1-acetyl-6-amino-2,3-dihydro-1H-indole (D10, 37.8 g, 0.22 mole), mechlorethamine hydrochloride (46 g, 0.24 mole) and anhydrous potassium carbonate (80 g, 0.58 mole) in 1-butanol (1800 ml) was heated at reflux for 8 h, then additional mechlorethamine hydrochloride (25 g, 0.13 mole) and potassium carbonate (41 g, 0.30 mole) were added and reflux continued for 3 h. The reaction mixture was allowed to cool and then washed with water (1000 ml). The aqueous wash was extracted with ethyl acetate, and the extract combined with the 1-butanol solution and concentrated in vacuo. The brown oily residue (60 g) was chromatographed on silica gel eluting with 0-8% MeOH/DCM to give an orange oil, which was trituated with ether to afford the title compound as a beige solid (12.2 g, 22%).

1. temperaturewas heated
2. temperatureat reflux for 8 h
3. temperaturereflux
4. temperatureto cool
5. washwashed with water (1000 ml)
6. washThe aqueous wash
7. extractionwas extracted with ethyl acetate
8. concentrationconcentrated in vacuo
9. customThe brown oily residue (60 g) was chromatographed on silica gel eluting with 0-8% MeOH/DCM
10. customto give an orange oil, which