Hydrochloric Acid → Olopatadine Impurity 54

HRID 1196999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196999
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([C:21]([O:23]C)=[O:22])=[CH:20][C:7]1=2.CO.[OH-].[Na+].Cl>O>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][C:7]1=2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 53998201Methyl 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Produkt 1

HCID 53645991Olopatadine Impurity 54Ausbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In this example, 26.1 g of methyl 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate is dissolved in a mixed solvent of 500 ml of methanol and 30 ml of water and 6.2 g of sodium hydroxide is added thereto. The mixture is heated at reflux for two hours. After allowing the mixture to stand for cooling, aqueous 4N-hydrochloric acid solution is added thereto to adjust the pH to 7 and the mixture is concentrated under reduced pressure. The concentrate is purified by column chromatography on high porous polymer (HP-20) (eluent: water:methanol=1:2) to obtain 25.0 g of the desired product.

Aufarbeitung

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureat reflux for two hours
  4. temperaturefor cooling
  5. concentrationthe mixture is concentrated under reduced pressure
  6. customThe concentrate is purified by column chromatography on high porous polymer (HP-20) (eluent: water:methanol=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-1e76260c1fa24a6fab40a18ed039d313
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116863

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