Tetrahydrofuran → 6-Acetylamino-2-(N,N-dimethylamino)methyltetralin

HRID 854023노트

반응식

HRID 854023 반응식
[CH2:1]1COCC1.[C:6]([NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=O)[CH2:15][CH2:14][CH2:13]2)(=[O:8])[CH3:7].[Cl-].C[CH:23]=[N+:24]=[CH:25]C>C(#N)C>[C:6]([NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([CH2:23][N:24]([CH3:25])[CH3:1])[CH2:14][CH2:13]2)(=[O:8])[CH3:7]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideHCID 21873455N,N-dimethylmethylene ammonium chloride

생성물 1

HCID 229985936-Acetylamino-2-(N,N-dimethylamino)methyltetralin

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A THF solution (40 ml) of 6-acetylamino-1-tetralone (1.692 g) was added to an acetonitrile solution (40 ml) of N,N-dimethylmethylene ammonium chloride (2.04 g), then stirred at room temperature for 24 hours, and concentrated. An aqueous solution of 10% potassium carbonate was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which was added sodium borohydride (0.86 g). The reaction mixture was stirred at room temperature for 1 hour, and water was added thereto, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which were added 10% palladium-carbon (0.4 g) and 1 N hydrochloric acid (20 ml). Then, this was catalytically reduced under a hydrogen pressure of 1 atmosphere, for 12 hours. The palladium-carbon was removed from the reaction mixture through filtration, the filtrate was concentrated, and an aqueous solution of 10% potassium carbonate was added thereto to form a free form compound. Then, this was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to obtain the entitled compound (1.862 g).

후처리

  1. concentrationconcentrated
  2. additionAn aqueous solution of 10% potassium carbonate was added to the residue, which
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in methanol (50 ml), to which
  8. additionwas added sodium borohydride (0.86 g)
  9. stirringThe reaction mixture was stirred at room temperature for 1 hour
  10. additionwater was added
  11. extractionwhich was then extracted with ethyl acetate
  12. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  13. customdried
  14. concentrationconcentrated
  15. dissolutionThe residue was dissolved in methanol (50 ml), to which
  16. additionwere added 10% palladium-carbon (0.4 g) and 1 N hydrochloric acid (20 ml)
  17. waitfor 12 hours
  18. customThe palladium-carbon was removed from the reaction mixture through filtration
  19. concentrationthe filtrate was concentrated
  20. additionan aqueous solution of 10% potassium carbonate was added
  21. customto form a free form compound
  22. extractionThen, this was extracted with ethyl acetate
  23. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  24. customdried
  25. concentrationconcentrated
  26. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-522d63fadd7b414d96346c3f65544cf4
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256204B2

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