1 CH3 N H2 N(CH3)2 * HCl O O O HC H / EtOH CH3 CH3 NaBH 4 / MeOH * HCl 1 N X 2 X=OH X=Cl DEL T N 2 ClCOOEt NaHCO3 Toluen 3 CH3 DEL T O COOEt (CO2) (CO2 ) (CH3 Cl) N t-BuOH , N O N NaOH / EtOH COOEt CH3 H N HCl O Cl N2 , CF 3 6 5 CF3 H OH 4 O CH3 CH3 CF3 CH3 H * HCl CH3 CH3 2 O O CH3 + (CH2O) x N Cl 1. B2 H6 2. SOCl2 3-dimethyloaminopropiophenone (I) F 3C N CH3 CH3 1. diborane 2. thionyl chloride CH3 CH3 dimethylamine paraformaldehyde acetophenone I + CH3 HN CH3 OH , NaOH II 4-trifluoromethylphenol N,N-dimethyl-3-phenyl3-chloropropylamine F3C F3C 1. BrCN 2. KOH O N CH3 O 1. cyanogen bromide N H CH3 Fluoxetine N,N-dimethyl-3-phenyl-3(4-trifluoromethylphenoxy)propylamine (II) CH3
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