Hydrochloric Acid → [3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone
Reaktionsgleichung
N([O-])=O.[Na+].N[C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:25]([N:27]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]3)=[O:26])[CH2:12]2)[O:8][N:7]=1.[ClH:34]>O>[Cl:34][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:25]([N:27]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]3)=[O:26])[CH2:12]2)[O:8][N:7]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of 332 mg (4.81 mmol) of sodium nitrite in 1.25 ml of water was added dropwise at 0° C. to a solution of 1.60 g (2.40 mmol) of the amine from Example 24A in 60% purity in 25 ml of concentrated hydrogen chloride solution. After the addition had ended, the mixture was stirred at 0° C. for 1 h and then at RT for 45 min. The reaction mixture was diluted with 1 N aqueous hydrogen chloride solution and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 220 mg (22% of theory)
Aufarbeitung
- additionAfter the addition
- waitat RT for 45 min
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by means of preparative HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-a59831364676486ebd72d4820987f90e
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08084469B2
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