(RS)-N,N-dimethyl-{2-[4-(alpha-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide → Cetirizine Hydrochloride

HRID 1072263

Reaktionsgleichung

Reaktionsgleichung von HRID 1072263
CN(C)[C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.C(N(CC)C(=O)C[O:35]CCN1CCN(C(C2C=CC=CC=2)C2C=CC([Cl:51])=CC=2)CC1)C>O1CCOCC1>[ClH:21].[ClH:51].[C:22]1([CH:14]([N:11]2[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][O:5][CH2:4][C:3]([OH:28])=[O:35])[CH2:9][CH2:10]2)[C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 10180126(RS)-N,N-dimethyl-{2-[4-(alpha-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamideHCID 22391920(RS)-N,N-diethyl-{2-[4-(alpha-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide

Produkt 1

HCID 55182Cetirizine HydrochlorideAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The procedure described in Example 14 is followed with the difference that, instead of the (RS)-N,N-dimethyl-{2-[4-(α-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide, 104.4 g (0.2 moles) of (RS)-N,N-diethyl-{2-[4-(α-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide are used, 100 ml of dioxane are employed as cosolvent, and, during the alkaline hydrolysis, the reaction mixture is boiled for 4 hours. Thus, 69.1 g (74.9%) of the title compound are obtained, m.p.: 225-228° C. The purity of the product corresponds to the quality requirements given in Eur. Pharm., 3, 1997, 1084.

Aufarbeitung

  1. customduring the alkaline hydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-daf8c77284af4de28b716c7be08bfd2d
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908999B2

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