Hydrochloric Acid → 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid
Reaktionsgleichung
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[C:24]=4[OH:31])[CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+].Cl.C(OCC)(=O)C>CO>[Cl:30][C:25]1[C:24]([OH:31])=[C:23]([CH:28]=[C:27]([Cl:29])[CH:26]=1)[CH2:22][N:19]1[CH2:18][CH2:17][CH:16]([CH2:15][NH:14][C:11]2[NH:10][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=2)[CH2:21][CH2:20]1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
After suspending 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid methyl ester (993 mg, 2.14 mmol) in methanol (10 ml), an aqueous lithium hydroxide solution (4M, 5.4 ml, 21.4 mmol) was added. The reaction mixture was stirred at 50° C. for 2 hours and then cooled to room temperature. 1N hydrochloric acid was added dropwise to adjust the pH to approximately 6.0. Ethyl acetate (1 ml) was then added and the mixture was stirred for 3 hours, after which the precipitate was filtered out to obtain 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid. The compound was identified by LC-MS.
Aufarbeitung
- temperaturecooled to room temperature
- stirringthe mixture was stirred for 3 hours
- filtrationafter which the precipitate was filtered out
Quellen und Nachweise
- ORD-Eintrag
- ord-d4ff95742a414f42a31dca2771f7e1ba
- Quelldatensatz
- uspto-grants-2009_04
- Patentnummer
- US07517875B2
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