Methanesulfonic Acid → Paroxetine Impurity 10

HRID 1108011

Reaktionsgleichung

Reaktionsgleichung von HRID 1108011
[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.[OH-].[K+].C1(NC(=O)[O-])C=CC=CC=1.[CH3:37][S:38]([OH:41])(=[O:40])=[O:39]>C1(C)C=CC=CC=1>[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].[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

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 14797Potassium HydroxideHCID 43815ParoxetineHCID 21896570Phenylcarbamate

Produkt 1

HCID 206527Paroxetine Impurity 10

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A round bottom flask was charged with unpurified paroxetine base (8.6 g) in toluene (20 ml) which had been prepared by potassium hydroxide hydrolysis of a phenylcarbamate derivative, and a solution of methanesulfonic acid (1.9 ml) in toluene (10 ml) was added dropwise. The resulting clear solution was placed into a separating funnel and extracted with water (30 ml). The aqueous phase was separated, residual toluene removed by evaporation at reduced pressure and the remaining clear solution (25 ml) was further diluted with water (40 ml). The water was removed by freeze drying to afford amorphous paroxetine methanesulfonate.

Aufarbeitung

  1. customThe resulting clear solution was placed into a separating funnel
  2. extractionextracted with water (30 ml)
  3. customThe aqueous phase was separated
  4. customresidual toluene removed by evaporation at reduced pressure
  5. additionthe remaining clear solution (25 ml) was further diluted with water (40 ml)
  6. customThe water was removed by freeze
  7. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-160d9eac20f045059b09b3fa6bc51c01
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063927

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