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

HRID 1166534

Reaction equation

HRID 1166534 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-03c15fedcc0548d2ab238ed924c81311
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Linked notes

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