Reaktionsgleichung
CNCCC(OC1C=CC(C(F)(F)F)=CC=1)C1C=CC=CC=1.Cl.[CH3:24][N:25]([CH3:36])[CH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].B#B>>[CH3:24][N:25]([CH2:26][CH2:27][CH:28]([OH:29])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:36]Komponenten
Versuchsvorschrift
In the process for the preparation of fluoxetine, as in U.S. Pat. No. 4,314,081, β-dimethylaminopropiophenone hydrochloride is used as a starting material which, after the liberation of the base, is hydrogenated with diborane, B2H4. The N,N-dimethyl-3-hydroxy-3-phenylpropylamine produced in the reaction is allowed to react with thionyl chloride in chloroform containing hydrochloric acid yielding N,N-dimethyl-3-phenyl-3-chloropropylamine. This compound is allowed to react under alkaline conditions with p-trifluoro-methylphenol by heating the mixture under reflux for 5 days and nights, after which N,N-dimethyl-3-p-trifluoromethylphenoxy-3-phenylpropylamine is produced. This compound is N-demethylated with the aid of cyanogen bromide, yielding N-methyl-N-cyano-3-(p-trifuoromethylphenoxy)-phenylpropylamine. The N-cyano group is removed from this compound by heating for 20 hours at 130° C. under reflux in a mixture of potassium hydroxide and ethylene glycol. The reaction mixture is extracted with ether and the ether phase is evaporated to dryness. The residue could further be transformed in a known manner into a pharmaceutically acceptable salt of fluoxetine.
Quellen und Nachweise
- ORD-Eintrag
- ord-6a6acbf10e9d48e18c50e2ffd34738cf
- Quelldatensatz
- uspto-grants-1992_11
- Patentnummer
- US05166437
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