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United States Patent Office Patiented Mar 3,171,838 United States Patent Office Patiented Mar. 2, 1965 2 To prepare the compounds of this invention, an appro 3, 7,838 priate aroylalkyl halide of the formula AEROYALKYL AN) HYDROXYARALKYL DERW ATIVES OF 4-(N-ARYLAYLEKANAMEDO)-PAPERE Ar-CO-Alk-halogen DSNES AND RELATED COMPOUNDS Paul A. J. Janssena, Wosselaar, near Teraho, Belgiu Ria, 5 is condensed with a piperidine of the formula assignor to Research Laboratorium Dr. C. Jai assera, H. N.V., Beerse, Belgia, a company of Belgium No Drawing. Fied Oct. 10, 1961, Ser. No. 144,017 A Caims. (C. 260-293.4) H'OX O The present invention relates to a novel group of com pounds which are derivatives of 4-anilinopiperidines. More particularly it relates to a group of compounds which can be represented by the following general for mula 5 wherein Ar, Alk and R are defined as above. The reac tion can be carried out in an inert solvent such as an H. aromatic hydrocarbon (e.g. benzene, toluene, Xylene), Ar-X-Alk-N X a lower alkanol (e.g. ethanol, propanol, butanol), and a lower alkanone (e.g. acetone, butanone, pentanone, hex 20 anone, and 4-methyl-2-pentanone). In certain cases the reaction can be usefully accelerated by use of elevated temperatures. The ketones thus obtained can be reduced with an appropriate reducing agent such as sodium boro hydride to give the alcohols of the present invention. 25 An alternate method for preparing the alkanols of the In this formula Ar is a member of the group consisting present inventions which can be used when Alk is methyl of pheny and thienyl; X is a member of the group con ene, involves heating styrene oxide with a substituted sisting of -CO-, -CHOH-, and piperidine which corresponds to the formula given above in the preparation of the ketones of this invention. >CHO(lower alkanoyl) 30 To prepare the intermediate piperidines described Alk is selected from the group consisting of methylene, above, 1-benzyl-4-piperidone is condensed with aniline ethylene, and alkyl methylene of less than 7 carbon to give N-(1-benzyl-4-piperidylidene)aniline. This com atoms; R is selected from the group consisting of lower pound is reduced to give 1-benzyl-4-anilinopiperidine alkyl, lower alkoxy, dimethylamino, morpholino, piper which can be reacted with an acid chloride or acid anhy idino, and 1-pyrrollidinyl. The lower alkanoyl radicals dride to give the corresponding amide, with an alkyl chlo referred to above are those derived from alkanoic acids roformate to give the corresponding urethane, or first with of less than 7 carbon atoms. The lower alkyl and lower phosgene and then with an appropriate secondary amine alkoxy radicals referred to above contain less than 7 car to give the corresponding urea. The N-benzyl group is bon atoms and include methyl, ethyl, propyl, butyl, amyl, then removed by hydrogenation over palladium on char hexyl, methoxy, ethoxy, propoxy, and butoxy. Illustra coal at atmospheric pressure. tive of the embodiments contemplated for Alk are methyl The compounds which constitute this invention and ene, ethylene, and alkyl methylenes of less than 7 carbon their preparation will appear more fully from a considera atoms, e.g., methyl methylene, ethyl methylene, propyl ion of the following examples which are given for the methylene, butyl methylene and the like. purpose of illustration only and are not to be construed The compounds of this invention are useful because 4.5 as limiting the invention in spirit or scope. In these of their valuable pharmacological properties. In particu examples, quantities are indicated in parts by weight, lar they are very potent analgesics and mydriatics. temperatures in degrees centigrade ( C.) and pressures The organic bases of this invention form pharmaceu in millimeters of mercury (mm). tically equivalent, non-toxic, acid-addition salts with a 50 Example I variety of organic and inorganic acids. Such salts are A mixture of 95 parts of 1-benzyl-4-piperidone, 60 parts formed with acids such as sulfuric, phosphoric, hydro of aniline, 800 parts of toluene, and 0.05 part of 4-toluene chloric, hydrobromic, hydriodic, sulfamic, citric, lactic, Sulfonic acid is refluxed in a vessel provided with a water maleic, malic, succinic, tartaric, cinnamic, acetic, benzoic, separator. After 15 hours the calculated amount of water gluconic, ascorbic and related acids. They also form 55 has separated and the mixture is cooled. The toluene is quaternary ammonium salts with a variety of organic esters evaporated and the residue is dissolved in 300 parts of of sulfuric, hydrohalic, and aromatic sulfonic acids. diisopropyl ether with stirring. The solution is filtered Among such salts are those formed with methyl chloride and the solvent is evaporated from the filtrate. Distilla and bromide, ethyl chloride, propyl chloride, butyl chlo tion of the residue gives N-(1-benzyl-4-piperidylidene)- ride, isobutyl chloride, benzyl chloride and bromide, phen 60 aniline boiling at about 170° C. at 0.05 mm. pressure. ethyl bromide, naphthylmethyl chloride, dimethylsulfate, A solution of 26 parts of N-(1-benzyl-4-piperidylidene) diethylsulfate, methyl benzenesulfonate, ethyl toluenesul aniline in 200 parts of ether is added portionwise to a fonate, ethylene chlorohydrin, propylene chlorohydrin, Suspension of 8 parts of lithium aluminum hydride and ally bronide, methalyl bromide and crotyl bromide. 200 parts of ether. The reaction mixture is stirred and re - 3,171,838 e - - 5 4. fluxed for 5 hours before it is cooled and decomposed by Example 4 the addition of 200 parts of water. The mixture is acidi To a solution of 15 parts of phosgene in 56 parts of fied with 100 parts of 12 N hydrochloric acid to give a toluene is added portionwise a solution of 13.3 parts of clear solution. The aqueous layer is separated and 64 1-benzyl-4-anilinopiperidine in 24 parts of toluene. The parts of tartaric acid is added to this solution with stir resultant mixture is stirred at room temperature for 20 ring. The resultant solution is made strongly alkaline minutes and then heated on a water bath for 2 hours. A and extracted with 3 portions of benzene. The organic solid precipitates from the cooled mixture, and it is filtered layer is dried over potassium carbonate and filtered and off and washed with diisopropyl ether and dried to give the solvent is evaporated. The resultant residue is recrys N-(1-benzyl-4-piperidyl)-N-phenylcarbamyl chloride hy tallized from petroleum ether to give 1-benzyl-4-anilino O drochloride, melting at about 178-185° C. This com piperidine melting at about 84.8-86 C. pound has the following formula - Example 2 To a solution of 19.5 parts of 1-benzyl-4-anilinopiperi dine in 160 parts of benzene is added portionwise a solu ( >-CH-OxY- N-C O-Cl tion of 10 parts of acetic anhydride and 40 parts of ben Zene with stirring. The mixture is refluxed for 3 hours before it is cooled and alkalized with sodium hydroxide solution. The organic layer is separated, washed with water, dried and filtered and the solvent is evaporated 20 from the filtrate. The residue is dissolved in petroleum To a stirred mixture of 60 parts of piperidine in 120 ether and crystallized from solution on cooling to give parts of benzene is added portionwise 25 parts of N-(1- N-(1-benzyl-4-piperidyl)-acetanilide melting at about benzyl-4-piperidyl)-N-phenylcarbamyl chloride hydro 107-109.2 C. with decomposition. This compound has chloride. The mixture is refluxed for 3 hours and then the following formula cooled, and 200 parts of water is added. The organic layer is separated, washed 3 times with 200 parts of water, dried over potassium carbonate and filtered, and the sol ( )-CH-Ox vent is evaporated. The residue is recrystallized from N-COCH petroleum ether to give N-(1-benzyl-4-piperidyl)-N-phen 30 yl-N',N'-pentamethyleneurea, melting at about 115-116 C. This compound has the following formula E. If the above procedure is repeated using propionic an 3 5 hydride in place of acetic anhydride and using a reflux C-on-OX C o-O period of 6 hours instead of 3 hours, the product ob tained is N-(1-benzyl-4-piperidyl)-propionanilide melting at about 74-76 C. If the procedure of the first paragraph is repeated using 40 butyric anhydride in place of acetic anhydride and using a reflux period of 16 hours instead of 3 hours the product is If equivalent quantities of the appropriate amine are N-(1-benzyl-4-piperidyl)-butyranilide. This amine is dis substituted for piperidine and the above procedure is re solved in diisopropylether and hydrogen chloride is passed peated, the following compounds are obtained: into the solution. The precipitated hydrochloride is 45 N - (1 - benzyl - 4 - piperidyl) - N - phenyl- N',N'- filtered, boiled in ethyl acetate, and filtered again to give tetramethyleneurea, melting at about 92-95.5° C. N-(1-benzyl-4-piperidyl) butyranilide hydrochloride melt N - (1 - benzyl - 4 - piperidyl) - N - phenyl- N',N'- dimethylurea, melting at about 99.8-101° C. ing at about 230-231° C. N - (1 - benzyl - 4 - piperidyl) - N - phenyl- N',N'- Example 3 50 (3-oxapentamethylene) urea, melting at about 104 31 parts of 1-benzyl-4-anilinopiperidine is stirred in 120 106° C. parts of pyridine at room temperature. To this solution Example 5 is added a solution of 18 parts of ethyl chloroformate in A solution of 16.5 parts of N-(1-benzyl-4-piperidyl) 32 parts of ether. After the addition is complete, the mix acetanilide in 160 parts of 2-propanol is hydrogenated ture is stirred at room temperature for 16 hours, and then 5 5 at atmospheric pressure and room temperature in the on the water bath at 60-65 C.
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