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

HRID 1072262

Reaktionsgleichung

Reaktionsgleichung von HRID 1072262
Cl.Cl.CN(C)[C:5](=[O:30])[CH2:6][O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.C(O)(=O)/C=C/C(O)=[O:36].CN(C)C(=O)COCCN1CCN(C(C2C=CC=CC=2)C2C=CC([Cl:60])=CC=2)CC1>>[ClH:23].[ClH:60].[C:24]1([CH:16]([N:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][O:7][CH2:6][C:5]([OH:30])=[O:36])[CH2:11][CH2:12]2)[C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

3

Edukt 2

HCID 22391908(RS)-N,N-dimethyl-{2-[4-(alpha-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide dihydrochlorideHCID 22391911(RS)-N,N-dimethyl-{2-[4-(alpha-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide fumarate

Produkt 1

HCID 55182Cetirizine HydrochlorideAusbeute 77,8 %

Versuchsvorschrift

The procedure described in Example 13 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 dihydrochloride, 106.4 g (0.2 moles) of (RS)-N,N-dimethyl-{2-[4-(α-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}-acetamide fumarate is used, and, after adjusting the pH of the reaction mixture to 3.8, the precipitated fumaric acid is filtered to facilitate the extraction with dichloromethane. Thus, 71.8 g (77.8%) 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. filtrationthe precipitated fumaric acid is filtered
  2. extractionthe extraction with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-39b56c52380e47fe8dc73857565a99ab
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908999B2

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