Sodium hydride → (+)-6-(4-Bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

HRID 382957

Reaction equation

HRID 382957 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH2:7]1)[CH3:3].[H-].[Na+].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][Cl:25])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.O>[ClH:25].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:16][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[CH2:7][CH:6]([CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])[CH2:15][CH2:14]3)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 68528p-Bromobenzyl chlorideHCID 21939715(+)-2-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralin

Product 1

HCID 18361483(+)-6-(4-Bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochlorideYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of (+)-2-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralin (9.2 g) in toluene (180 ml) was added sodium hydride (60% in oil, 2.0 g). After stirring at 50° C. for 30 min, a solution of 4-bromobenzyl chloride (9.7 g) in toluene (45 ml) was added to the reaction mixture, which was heated under reflux for one hr. The reaction mixture was diluted with water and concentrated. The residue 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 dissolved in solvent mixture of ethyl acetate/hexane (1:4) and the precipitate was filtered off. The filtrate was concentrated and the residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:50 to 1:4) and converted into its hydrochloride. The crystals were washed with diisopropyl ether to obtain the titled compound (17.0 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hr
  3. concentrationconcentrated
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. customdried
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in solvent mixture of ethyl acetate/hexane (1:4)
  10. filtrationthe precipitate was filtered off
  11. concentrationThe filtrate was concentrated
  12. customthe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:50 to 1:4)
  13. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-4c8edf62d7974c13ad1af4beaa6e432f
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Linked notes

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