Sodium Chloride → 6-(3'-Aminobiphenyl-4-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

HRID 1166534

Reaktionsgleichung

Reaktionsgleichung von HRID 1166534
[NH2:1][C:2]1[CH:3]=[C:4](OB(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:19]1[CH:41]=[CH:40][C:22]([CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH:30]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[CH2:29][CH2:28]3)=[CH:21][CH:20]=1.[Cl-:42].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C>[ClH:42].[NH2:1][C:2]1[CH:7]=[C:6]([C:19]2[CH:41]=[CH:40][C:22]([CH2:23][O:24][C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][CH:30]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[CH2:29][CH2:28]4)=[CH:21][CH:20]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 183614846-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralinHCID 218958363-Aminophenylboric acid

Produkt 1

HCID 183615236-(3'-Aminobiphenyl-4-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

An ethanol solution (10 ml) of 3-aminophenylboric acid (1.3 g) and an aqueous 2M sodium carbonate solution (10 ml) were added to a toluene solution (80 ml) of 6-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino) ethyl]tetralin (3.00 g) and tetrakis-(triphenylphosphine) palladium (0.45 g). The reaction mixture was heated under reflux for 12 hours in an argon atmosphere. A saturated aqueous sodium chloride solution was added to this, which was then extracted with ethyl acetate. The organic layer was dried, and then concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/2), and then processed with 4 N hydrochloric acid-ethyl acetate to form a hydrochloride. The thus-formed salt was recrystallized from methanol-diisopropyl ether to obtain the entitled compound (0.78 g).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 hours in an argon atmosphere
  3. extractionwas then extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-03c15fedcc0548d2ab238ed924c81311
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613805B2

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