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

HRID 382957

반응식

HRID 382957 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c8edf62d7974c13ad1af4beaa6e432f
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310107B1

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