Methanesulfonic Acid → Paroxetine Impurity 10

HRID 1108010

Reaktionsgleichung

Reaktionsgleichung von HRID 1108010
[CH:1]1[C:6]([C@H:7]2[C@H:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]4[O:23][CH2:22][O:21][C:19]=4[CH:20]=3)[CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:5][CH:4]=[C:3](F)[CH:2]=1.[CH3:25][S:26]([OH:29])(=[O:28])=[O:27]>CC(O)C>[CH3:25][S:26]([OH:29])(=[O:28])=[O:27].[CH2:8]1[C@@H:7]([C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)[C@H:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][O:21][C:19]=3[CH:20]=2)[CH2:11][NH:10][CH2:9]1

Komponenten

4

Edukt 2

HCID 6395Methanesulfonic AcidHCID 43815Paroxetine

Produkt 1

HCID 206527Paroxetine Impurity 10

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

A round bottomed flask was charged with a solution of paroxetine base (23.5 g) in toluene (50 ml), obtained directly from the base hydrolysis of the N-phenoxycarbonyl intermediate. The toluene was removed in vacuo to produce an oily residue. To this residue was added propan-2-ol (50 ml) and the mixture was warmed to ensure total dissolution of the paroxetine. The temperature of the solution was cooled to 18° C. and methanesulfonic acid (6.86 g) was added, then the solvents were removed at reduced pressure and replaced with fresh propan-2-ol (110 ml). The solution was heated to reflux temperature, cooled to 18° C., and seeded with crystalline paroxetine methanesulfonate. Crystallisation was induced with vigorous stirring and insonation, and the product collected by filtration, and dried over phosphorus pentoxide in a vacuum desiccator to produce paroxetine methanesulfonate as a white crystalline solid.

Aufarbeitung

  1. customThe toluene was removed in vacuo
  2. customto produce an oily residue
  3. temperaturethe mixture was warmed
  4. customthe solvents were removed at reduced pressure
  5. temperatureThe solution was heated
  6. temperatureto reflux temperature
  7. temperaturecooled to 18° C.
  8. customCrystallisation
  9. filtrationinsonation, and the product collected by filtration
  10. dry with materialdried over phosphorus pentoxide in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-f10f26c42e574536b2ec6eed38086489
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063927

Verknüpfte Notizen

Wird geladen…