4-Chloro-p-fluoro-butyrophenone

A mixture of 3.2 parts 4-chloro-p-fluoro-butyrophenone, 3.5 parts 1-oxo-4-phenyl-2,4,8-triazaspiro(4,5)decane, 2 parts Na COs hd 0.1 part Kl in 200 parts hexone is refluxed with stirring for 50 hours. The mixture is cooled to room temperature, 200 parts water are added and the layers are separated. The organic layer is dried over 10 parts MgSO, ... 

A mixture of 3.2 parts 4-chloro-p-fluoro-butyrophenone, 3.5 parts l-oxo-4-phenyl-2,4,8-triazaspiro(4,5)decane, 2 parts Na2C03 and 0.1 part KI in 200 parts hexone is refluxed with stirring for 50 hours. The mixture is cooled to room temperature, 200 parts water are added and the layers are separated. The organic layer is dried over 10 parts MgS04, filtered and the solvent removed under reduced pressure on the water bath. The residue is treated with 50 parts diisopropylether. The precipitate is filtered on a Buchner filter and recrystallized from 20 parts hexone at room temperature. The solid is filtered off and dried to yield l-oxo-4-phenyl-8-[3-(4-fluorobenzoyl)-propyl] -2,4,8-triazaspiro(4.5)decane, melting point 190° to 193.6°C, as a light brown amorphous powder. 

A mixture of 6.6 parts of y-chloro-p-fluoro-butyrophenone and 12.5 parts of 1-(o-anisyl)piperazine is heated for 10 hours at a temperature of 110°C. The reaction mixture is treated with 800 parts of ether and filtered. The ether layer is washed with water, dried over anhydrous potassium carbonate and filtered, whereupon hydrogen chloride gas is introduced into the solution. The precipitate is collected on a filter and dissolved in a mixture of 240 parts of 2-propanol and 80 parts of acetone to yield l-[y-(p-fluorobenzoyl)propyl]-4-(o-... 

A solution or dispersion consisting of 20.1 g (0.1 mol) of y-chloro-p-fluorobutyrophenone, 19.8 g (0.2 mol) of 4-methylpiperidine and 0.1 g of potassium iodide in 150 ml toluene is heated in a sealed glass tube for 15 hours at 100°C to 110°C. The potassium iodide and the 4-methylpiperidine hydrochloride formed in the reaction are separated by filtration and the solvent removed from the filtrate by evaporation in vacuum on a steam bath. The residue is distilled and the fraction obtained at 120°C to 125°C and at a pressure lower than 0.1 mm Hg is collected. The base is dissolved in ether and the 4-fluoro-y-(4-methylpiperidino)-butyrophenone precipitated as the hydrochloride. The reaction product is purified by recrystallization in ethanol/ether. 

Pipamperone, I. [4.(4-Fluorophenyl)-4-oxobut-< - 1,4 -bipiperidineJ-4 -carboxamide 1 -[3-(p-fluoro-benzoyl)propyl]-[I,4 -bipiperidine]-4 -carboxamide l -ip-fluorophenyl)-4-(4 -piperidino-4 -carbamoylpiperidino)-l butanone l [7-(4-fluorobenzoyl)propyl] -4-piperidinopiper-idine-4-carboxamide 4 -fluoro-4-(/V-[4-(lV-piperidino)-4-carbamido]piperidino]butyrophenone floropipamide R 3345 Dipiperon Piperonyl Prop tan C1,H30FNjOj mol wt 375,49. C 67.17%, H 8.05%, F 5.06%, N 11.19%, 6 8.52%. Prepn of the dihydrochloride by reaction of y-chloro-4-fluorobutyrophenone and 4-piperidinopiperidine-4-carbox-... 

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