Phosphorus oxychloride → 2-(3,4-Dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 1358018노트

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HRID 1358018 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=2)[C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Cl)(Cl)(Cl)=O.[BH4-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:20][CH2:21][C:22]3[C:27](=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=3)[CH:10]2[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 23440903N-(3,4-Dichlorophenyl)-2-(4-hydroxyphenyl)-N-(2-[3-(phenylmethoxy)phenyl]ethyl}acetamide

생성물 1

HCID 234407442-(3,4-Dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline수율 6.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a solution of N-(3,4-dichlorophenyl)-2-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl}acetamide (7.6 g, 0.015 mol) in acetonitrile (30 ml) was added phosphorus oxychloride (4.19 ml, 0.045 mol). The reaction was allowed to reflux at 80° C. for 6 hours. Solvent was removed and the reaction was placed on ice. To the flask was added ice and water. The reaction was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated, and then dissolved in methanol. To the flask was added small aliquots of sodium borohydride (1.02 g, 0.027 mol). The reaction was allowed to stir overnight. The solvent was removed and the reaction was diluted with dichloromethane and water. The organic layer was separated and the aqueous layer was extracted with additional dichloromethane. The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound (0.5 g, 6.8% yield): ES-MS (m/z) 490 [M+H]+.

후처리

  1. customSolvent was removed
  2. additionTo the flask was added ice and water
  3. extractionThe reaction was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutiondissolved in methanol
  9. customThe solvent was removed
  10. additionthe reaction was diluted with dichloromethane and water
  11. customThe organic layer was separated
  12. extractionthe aqueous layer was extracted with additional dichloromethane
  13. washwashed with brine
  14. dry with materialdried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ad80550de85a41509e9dc16e7bb2ebbc
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593322B1

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