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HRID1016374

反应详情

EQUATION

反应方程式

HRID 1016374 的结构方程式

REACTANTS

反应物

3
结构：C1CCOC1
HCID8028

Tetrahydrofuran

C4H8O

结构：CSCS(C)=O
HCID99129

Methane, (methylsulfinyl)(methylthio)-

C3H8OS2

结构：O=Cc1cnc2n1CCc1ccccc1C2=C1CCN(CCc2ccc(OCc3ccc4ccccc4n3)cc2)CC1
HCID9915664

未命名化合物

PRODUCTS

生成物

1
结构：COC(=O)Cc1cnc2n1CCc1ccccc1C2=C1CCN(CCc2ccc(OCc3ccc4ccccc4n3)cc2)CC1
HCID18612504

未命名化合物

收率 30%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C[N+](C)(C)Cc1ccccc1.[OH-]
溶剂HCID66854

Benzyltrimethylammonium hydroxide

C10H17NO

PROCEDURE

实验过程

A mixture of compound 4 (8.32 g) and methyl methylthiomethyl sulfoxide (MMTS) (4.5 g) in THF (100 ml) and benzyltrimethyl ammonium hydroxide (40% in methanol; 20 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was taken up in water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. Toluene was added twice and evaporated again. The residue was taken up in methanol (50 ml). HCl gas was bubbled through the mixture, cooled on an ice bath, for 30 minutes. The mixture was stirred overnight. The solvent was evaporated. The residue was taken up in water, alkalized with K2CO3 and extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 2.7 g (30%) of methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)-phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-acetate (compound 5).

WORKUP

后处理

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. additionToluene was added twice
  9. customevaporated again
  10. customHCl gas was bubbled through the mixture
  11. temperaturecooled on an ice bath, for 30 minutes
  12. stirringThe mixture was stirred overnight
  13. customThe solvent was evaporated
  14. extractionextracted with DCM
  15. customThe organic layer was separated
  16. customdried
  17. filtrationfiltered
  18. customthe solvent was evaporated
  19. customThe residue was purified over silica gel on a glass
  20. filtrationfilter (eluent CH2Cl2/CH3OH 95/5)
  21. customThe pure fractions were collected
  22. customthe solvent was evaporated
  23. customThe residue was crystallized from ACN
  24. filtrationThe precipitate was filtered off
  25. customdried