Ethanol → (+)-2-[2-(N,N-Dimethylamino)ethyl]-6-[4-(2-naphthyl)phenyl]methoxytetralin hydrochloride

HRID 382978Notes

Reaction equation

HRID 382978 reaction equation
[ClH:1].Br[C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:33](O)[CH3:34].[C:36](=O)([O-])[O-].[Na+].[Na+]>O.[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>[ClH:1].[CH3:22][N:21]([CH2:20][CH2:19][CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][C:6]3[CH:24]=[CH:25][C:3]([C:28]4[CH:29]=[CH:30][C:31]5[C:26](=[CH:32][CH:36]=[CH:33][CH:34]=5)[CH:27]=4)=[CH:4][CH:5]=3)[CH:10]=2)[CH2:15]1)[CH3:23]

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 18361483(+)-6-(4-Bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

Product 1

HCID 18361577(+)-2-[2-(N,N-Dimethylamino)ethyl]-6-[4-(2-naphthyl)phenyl]methoxytetralin hydrochloride

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of (+)-6-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride (1 g), toluene (20 ml), ethanol (2.5 ml), and 2 M aqueous sodium carbonate (2.5 ml) was stirred at room temperature for 10 min. 2-Naphthaleneboric acid (526 mg) and tetrakis(triphenylphosphine) palladium (82 mg) were added and the reaction mixture was heated under reflux for 14 hr under argon. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:20 to 1:7) and converted into its hydrochloride, which was then recrystallized from methanol-diisopropyl ether to obtain the titled compound (850 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 14 hr under argon
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:20 to 1:7)
  9. customwas then recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-6e3ee476f8dc4220ba5719034d99e772
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Reaction notes

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