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Tetrahydrofuran → 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

HRID 1625165
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HRID 1625165 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[O:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C@H:18]3[C:19](=[O:23])[N:20]([CH3:22])[CH2:21][C@@H:17]3[C:16]=2[CH:31]=1.[OH-:32].[Na+].[O:34]1CCCC1>>[CH3:22][N:20]1[CH2:21][CH:17]2[CH:18]([C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[O:26][C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:31][C:16]=32)[CH2:19]1.[CH:18](/[C:19]([OH:23])=[O:34])=[CH:24]/[C:25]([OH:26])=[O:32]
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6

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HCID 8028Tetrahydrofuran2회HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 58729182(3aS,12bS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

생성물 1

HCID 11954293
5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

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온도
5 °C

실험 절차

Aluminum chloride (2.7 g) is added to tetrahydrofuran (60 mL) at 25-30° C. The solution is cooled to 0-10° C. and lithium aluminum hydride (1.08 g) is added. The mixture is stirred for 15-30 minutes. A solution of trans-5-chloro-2,3,3a,12b-tetra hydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (6.0 g) in tetrahydrofuran (120 mL) is added drop-wise at 0-10° C. and the mixture is maintained for 1 hour. Sodium hydroxide solution (0.6N, 100 mL) is added at 0-10° C. The mixture is extracted with ethyl acetate (75 mL) and layers are separated, then the aqueous layer is washed with ethyl acetate (25 mL). The combined organic layer is washed with saturated brine solution (2×100 mL). The organic layer is dried over anhydrous sodium sulfate (10 g) and the solvent from the organic layer is evaporated at 45° C. The obtained residue is dissolved in 1-propanol (20 mL) at 25-30° C. This solution is added to a solution of maleic acid (3.2 g) in 1-propanol (10 mL) at 25-30° C. and stirred for 10 minutes, then seeded with asenapine maleate monoclinic form (120 mg). The mixture is stirred at 25-35° C. for 24 hours and the obtained solid is collected by filtration, washed with 1-propanol (5 mL), and dried under reduced pressure at 65° C., to afford 4.9 g of the title compound. Purity by HPLC: 99.59%; PXRD pattern is shown as FIG. 1; endotherm by DSC: 147° C.; weight loss by TGA: 0.04%; moisture content by Karl Fischer (KF): 0.12%; residual solvents: 1-propanol: 150.3 ppm; ethyl acetate: not detected; tetrahydrofuran: not detected; particle size distribution: d(10)=5.671 μm, d(50)=24.077 μm, d(90)=58.716 μm.

후처리

  1. temperaturethe mixture is maintained for 1 hour
  2. extractionThe mixture is extracted with ethyl acetate (75 mL) and layers
  3. customare separated
  4. washthe aqueous layer is washed with ethyl acetate (25 mL)
  5. washThe combined organic layer is washed with saturated brine solution (2×100 mL)
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate (10 g)
  7. customthe solvent from the organic layer is evaporated at 45° C
  8. dissolutionThe obtained residue is dissolved in 1-propanol (20 mL) at 25-30° C
  9. additionThis solution is added to a solution of maleic acid (3.2 g) in 1-propanol (10 mL) at 25-30° C.
  10. stirringstirred for 10 minutes
  11. stirringThe mixture is stirred at 25-35° C. for 24 hours
  12. filtrationthe obtained solid is collected by filtration
  13. washwashed with 1-propanol (5 mL)
  14. customdried under reduced pressure at 65° C.

출처 및 근거

ORD 기록
ord-47c19cad81414f09b36a360e675814e6
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08779161B2

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