Sodium Chloride → 2-(N,N-Dimethylamino)methyl-6-(4'-methoxybiphenyl-4-yl)methoxytetralin hydrochloride

HRID 382966Notes

Reaction equation

HRID 382966 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-:42].[Na+]>C1(C)C=CC=CC=1.[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.C(O)C>[ClH:42].[CH3:20][N:19]([CH2:18][CH:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH2:6][C:5]3[CH:22]=[CH:23][C:2]([C:29]4[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=4)=[CH:3][CH:4]=3)[CH:9]=2)[CH2:14]1)[CH3:21]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acidHCID 183615356-(4-Bromobenzyl)oxy-2-(N,N-dimethylamino)methyltetralin

Product 1

HCID 183615702-(N,N-Dimethylamino)methyl-6-(4'-methoxybiphenyl-4-yl)methoxytetralin hydrochloride

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

6-(4-Bromobenzyl)oxy-2-(N,N-dimethylamino)methyltetralin (374 mg; obtained in Reference Example 33) and tetrakis-(triphenylphosphine) palladium (35 mg) were dissolved in toluene (8 ml), to which were added an ethanol solution (1 ml) of 4-methoxyphenylboric acid (198 mg) and an aqueous 2 M sodium carbonate solution (1 ml). The reaction mixture was heated under reflux for 6 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=1/10), and then processed with 4 N hydrochloric acid-ethyl acetate to form a hydrochloride. The thus-formed salt was recrystallized from ethanol-ethyl acetate to obtain the entitled compound (0.290 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 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=1/10)

Sources & evidence

ORD record
ord-4f4c32ab81f848f0987f95f9e7e2f4c8
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Reaction notes

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