반응 #82427

반응 방정식

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

수율 75.0%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   온도The solution was heated
2. 2
   온도to reflux for 2 h
3. 3
   기타the solvent removed in vacuo
4. 4
   여과The residue was filtered through silica gel
5. 5
   세척eluted with 25% ethyl acetate in hexanes
6. 6
   농축After concentration under reduced pressure, methanol (20 mL)
7. 7
   workup.ADDITIONwas added
8. 8
   온도the solution was heated
9. 9
   온도to reflux for 30 minutes, before the solvent
10. 10
    기타was removed in vacuo
11. 11
    기타The product was crystallized from ethanol/ether
12. 12
    기타to give 0.46 g

실험 절차

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).

출처