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

HRID 1166532Notes

Reaction equation

HRID 1166532 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-2cd8f4e88bb84496ba9e8c99c281bcbc
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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