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

HRID 54149

Reaktionsgleichung

Reaktionsgleichung von HRID 54149
C([N:8]1[CH2:16][C:15]2[C:14]3[CH:17]=[CH:18][C:19]([O:23][CH3:24])=[C:20]([O:21][CH3:22])[C:13]=3[CH2:12][CH:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:47]C(OC(Cl)C)=O>ClCCCl>[ClH:47].[CH3:22][O:21][C:20]1[C:13]2[CH2:12][CH:11]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:10]3[CH2:9][NH:8][CH2:16][C:15]=3[C:14]=2[CH:17]=[CH:18][C:19]=1[O:23][CH3:24]

Komponenten

5

Edukt 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 199611422-benzyl-6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole

Produkt 1

HCID 199610916,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro 1H-benz[e]isoindole hydrochlorideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 h
  3. customthe solvent removed in vacuo
  4. filtrationThe residue was filtered through silica gel
  5. washeluted with 25% ethyl acetate in hexanes
  6. concentrationAfter concentration under reduced pressure, methanol (20 mL)
  7. additionwas added
  8. temperaturethe solution was heated
  9. temperatureto reflux for 30 minutes, before the solvent
  10. customwas removed in vacuo
  11. customThe product was crystallized from ethanol/ether
  12. customto give 0.46 g

Quellen und Nachweise

ORD-Eintrag
ord-5c760c5b0fdc40ee939b2fb1b7effd11
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621133

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