Ammonium Chloride → alpha-(1-Methyl-4-piperidyl)-2-(2,5-difluorophenylthio)-5-methoxybenzyl alcohol
Reaktionsgleichung
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[S:18][C:19]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:20]=1[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([CH:21]([OH:22])[C:20]2[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:19]=2[S:18][C:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=2[F:10])[CH2:3][CH2:4]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of a Grignard reagent is prepared by a reaction of 6.7 g of 4-chloro-1-methylpiperidine with 1.25 g of magnesium in 40 ml of tetrahydrofuran and is treated while stirring for 10 minutes with a solution of 9.35 g 2-(2,5-difluorophenylthio)-5-methoxy-benzaldehyde in 20 ml of tetrahydrofuran, added dropwise. The mixture is refluxed for 3 hours and, after cooling, it is decomposed with a 20% ammonium chloride solution and extracted with benzene. The extract is washed with water, dried with potassium carbonate and evaporated. There are obtained 12.6 g (100%) of crude oily α-(1-methyl-4-piperidyl)-2-(2,5-difluorophenylthio)-5-methoxybenzyl alcohol which is used in this state for the next reaction. For characterization the crystalline hydrogen oxalate may be prepared by neutralization of a sample with oxalic acid; it is purified by crystallization from acetone and melts at 160°-163° C.
Aufarbeitung
- additionis treated
- additionadded dropwise
- temperatureThe mixture is refluxed for 3 hours
- temperatureafter cooling
- extractionextracted with benzene
- washThe extract is washed with water
- dry with materialdried with potassium carbonate
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-b865e5c04b0842d2b4ff341c8bbfda82
- Quelldatensatz
- uspto-grants-1984_02
- Patentnummer
- US04431808
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