Reaktion #82427

Reaktionsgleichung

2-benzyl-6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole

1,8-bis(dimethylamino)-naphthalene

1-chloroethyl chloroformate

→

6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole hydrochloride

Ausbeute 75.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was heated
2. 2
   Temperaturto reflux for 2 h
3. 3
   Sonstigethe solvent removed in vacuo
4. 4
   FiltrationThe residue was filtered through silica gel
5. 5
   Wascheneluted with 25% ethyl acetate in hexanes
6. 6
   EinengenAfter concentration under reduced pressure, methanol (20 mL)
7. 7
   workup.ADDITIONwas added
8. 8
   Temperaturthe solution was heated
9. 9
   Temperaturto reflux for 30 minutes, before the solvent
10. 10
    Sonstigewas removed in vacuo
11. 11
    SonstigeThe product was crystallized from ethanol/ether
12. 12
    Sonstigeto give 0.46 g

Vorschrift

To a solution of 1.0 g (2.52 mmol) of 2-benzyl-6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole, from Step 5, in 22 mL of 1,2-dichloroethane was added 0.11 g (0.05 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.33 mL (3.15 mmol) of 1-chloroethyl chloroformate at 0° C. The solution was heated to reflux for 2 h and the solvent removed in vacuo. The residue was filtered through silica gel eluted with 25% ethyl acetate in hexanes. After concentration under reduced pressure, methanol (20 mL) was added and the solution was heated to reflux for 30 minutes, before the solvent was removed in vacuo. The product was crystallized from ethanol/ether to give 0.46 g. (75% yield) of 6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole hydrochloride as a white solid.; MS DCI: 308 (M+H)+ ; 1H NMR (d6 -DMSO) δ: 3.05-3.25 (m, 2H), 3.55 (s, 3H), 3.80 (s, 3H), 3.88 (m, 1H), 4.0-4.15 (m, 2H), 4.25-4.45 (m, 2H), 6.91 (m, 1H), 7.15-7.3 (m, 3H), 7.4-7.6 (m, 3H).

Quelle