Ethanol → HCID 69117886, compound

HRID 854048Notes

Reaction equation

HRID 854048 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(C)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:33]([OH:35])C.[C:36](=O)([O-])[O-:37].[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].[CH3:36][O:37][C:27]1[CH:28]=[C:29]([C:3]2[CH:25]=[CH:24][C:6]([CH2:7][O:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[CH2:15][CH:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:13][CH2:12]4)=[CH:5][CH:4]=2)[CH:30]=[CH:31][C:26]=1[O:35][CH3:33]

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 69117886HCID 69117886, 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. 3.4-Dimethoxybenzeneboric acid (557 mg) and tetrakis(triphenylphosphine) palladium (82 mg) were added and the reaction mixture was heated under reflux for 5 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 1:5) and converted into its hydrochloride, which was then recrystallized from methanol-diisopropyl ether to obtain the titled compound (840 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 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 1:5)
  9. customwas then recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-147f25cd03714b528acda4abcac2196d
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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