Potassium Iodide → 6-Desfluoro-6-hydroxy Risperidone

HRID 1472629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472629
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]2[C:26]3[CH:27]=[CH:28][C:29]([OH:31])=[CH:30][C:25]=3[O:24][N:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C=O)C.O>[OH:31][C:29]1[CH:28]=[CH:27][C:26]2[C:22]([CH:19]3[CH2:18][CH2:17][N:16]([CH2:2][CH2:3][C:4]4[C:9](=[O:10])[N:8]5[CH2:11][CH2:12][CH2:13][CH2:14][C:7]5=[N:6][C:5]=4[CH3:15])[CH2:21][CH2:20]3)=[N:23][O:24][C:25]=2[CH:30]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27630793-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4hpyrido(1,2-a)pyrimidin-4-oneHCID 1363771963-(Piperidin-4-yl)benzo[d]isoxazol-6-ol

Produkt 1

HCID 1356880556-Desfluoro-6-hydroxy Risperidone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (14.4 g, 0.05 mmol), 3-(piperidin-4-yl)benzo[d]isoxazol-6-ol (14.0 g, 0.05 mmol), sodium carbonate (16.0 g, 0.15 mmol) and potassium iodide (spatula point) in DMF (150 mL) was stirred for 5 h at 80° C. The mixture was allowed to cool down to room temperature and water was added. The precipitate was removed by filtration, and the filtrate was extracted with chloroform (3×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was crystallized with isopropyl alcohol (70 mL), filtered, and washed with isopropanol/diisopropyl ether 50/50 mixture (10 mL). The residue was dried overnight at 100° C. yielding the title compound and was used without further purification in the next step.

Aufarbeitung

  1. customThe precipitate was removed by filtration
  2. extractionthe filtrate was extracted with chloroform (3×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized with isopropyl alcohol (70 mL)
  7. filtrationfiltered
  8. washwashed with isopropanol/diisopropyl ether 50/50 mixture (10 mL)
  9. customThe residue was dried overnight at 100° C.

Quellen und Nachweise

ORD-Eintrag
ord-4f1f5091b13c40da93700751d3bce719
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012648B2

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