1,4-Dioxane → Cetirizine

HRID 1003751

Reaktionsgleichung

Reaktionsgleichung von HRID 1003751
[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH2:17][CH2:16]2)[C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.Cl.[O:28]1CCOCC1>[OH-].[Na+].O=O.[Pt]>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][O:23][CH2:24][C:25]([OH:28])=[O:26])[CH2:19][CH2:20]2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 2

HCID 312751,4-DioxaneHCID 71612Hydroxyzine monohydrochloride

Produkt 1

HCID 2678CetirizineAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 977OxygenLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a stirred and heated (80° C.) suspension of hydroxyzine hydrochloride (1.0 g, 2.23 mmol) and 5% Pt/C in dioxane (10 mL) and 1N aqueous NaOH solution (10 mL), O2 was bubbled through for 20 hours. After being cooled down to room temperature, The mixture was filtered through a pad of celite (2.5×2 cm) and washed with water. The filtrate was extracted with dichloromethane (3×25 mL). The combined organic solution was dried (Na2SO4). Evaporation of solvent gave the titled compound as a pale white form (0.51 g, yield 58.7%).

Aufarbeitung

  1. temperatureheated
  2. customwas bubbled through for 20 hours
  3. filtrationThe mixture was filtered through a pad of celite (2.5×2 cm)
  4. washwashed with water
  5. extractionThe filtrate was extracted with dichloromethane (3×25 mL)
  6. dry with materialThe combined organic solution was dried (Na2SO4)
  7. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-daae75fdb6f64db39be62055c3f5818e
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046332

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