Ethanol → HCID 18361527, compound

HRID 854050Notes

Reaction equation

HRID 854050 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]([OH:35])C.C(=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].[O:35]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:32]=[C:33]1[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

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 18361527HCID 18361527, compound

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-Benzofuranboric acid (496 mg) and tetrakis(triphenylphosphine) palladium (82 mg) were added and the reaction mixture was heated under reflux for 6 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 crude crystals were washed with diisopropyl ether and further purified by alumina column chromatography (eluent:ethyl acetate) and converted into its hydrochloride, which was then recrystallized from methanol-diisopropyl ether to obtain the titled compound (730 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 6 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. washThe crude crystals were washed with diisopropyl ether
  9. customfurther purified by alumina column chromatography (eluent:ethyl acetate)
  10. customwas then recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-ab39d450bab94342903b1b1144fae511
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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