Toluene → HCID 18361476, compound

HRID 854045Notes

Reaction equation

HRID 854045 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.C(=O)([O-])[O-].[Na+].[Na+].B(O)(O)O.CC1C=CC=CC=1>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.C(O)C>[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:29]4[CH:30]=[CH:31][C:26]([CH3:32])=[CH:27][CH:28]=4)=[CH:4][CH:5]=3)[CH:10]=2)[CH2:15]1)[CH3:23]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 18361483(+)-6-(4-Bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochlorideHCID 187641984-Methylbenzeneboric acid

Product 1

HCID 18361476HCID 18361476, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 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. 4-Methylbenzeneboric acid (416 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=1:40 to 1:4) and converted into its hydrochloride, which was then recrystallized from methanol-diisopropyl ether to obtain the titled compound (660 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=1:40 to 1:4)
  9. customwas then recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-4f86ed99382d40f681e634623cf41cb5
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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