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|Spotion Analgesic Aetion and May Be Used As Substitutes (CH3)2C-CHCH.N(CH3), (CH3):NH (C.H.G-HCH,61 for Morphine

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|Spotion Analgesic Aetion and May Be Used As Substitutes (CH3)2C-CHCH.N(CH3), (CH3):NH (C.H.G-HCH,61 for Morphine Patented Mar. 9, 1954 2,671,798 UNITED STATES PATENT OFFICE 2,2-DIPHENYL-3-METHYL - 4 - CHLORO BUTYRONTRLE AND PROCESSES FOR PRE PARING THE SAME Earl M. Chamberlin and Max Tishler, Westfield, N. J., assignors to Merck & Co., Inc., Rahway, N. J., a corporation of New Jersey No Drawing. Original application April 9, 1949, Serial No. 86,596. Divided and this application July 25, 1951, Seria No. 238,576 Y 6 Claims. (C. 260-465) i 2 This invention relates o the manufacture of duce 2,2-diphenyl-3-methyl-4-chlorobutyrohi. compounds possessing analgesic and anesthetic trile (compound 4) which is reacted with dimeth action. In particular, it is concerned with an im ylamine to form 2,2-diphenyl-3-methyl-di proved Synthetic method for preparing 2,2-di methylamino-butyronitrile (compound 5). These phenyl-3-methyl-4-dimethylamino-butyronitrile reactions niay be chemically represented as for and with novel chemical compounds useful as OWS: intermediates in the preparation of this com pound. 2,2-diphenyl-3-methyl-4-dimethylami CH3CHOHCHC - RSOCl - CH 6HCH Gl no-butyronitrile is itself an important intermedi Ösor ate in the synthesis of isoamidone, 1-dimethyl O (1) (2) (3) amino-2-methyl-3,3-diphenyl-hexanone-4 and salts thereof. Isoamidone and its salts possess |Spotion analgesic aetion and may be used as substitutes (CH3)2C-CHCH.N(CH3), (CH3):NH (C.H.G-HCH,61 for morphine. C ÖH, {SS o6. bH, This application is a division of our co-pending 5 application Serial No. 86,596, filed April 9, 1949, (5) (4) now Patent No. 2,607,794. The organic sulfonyl chloride employed in the 2,2-diphenyl-3-methyl - 4 - dimethylamino-bu foregoing reaction can be either an aromatic tyronitrile has been prepared previously by react sulfonyl chloride such as p-toluene sulfonyl ing 1-dimethylamino-2-chloropropane with di 20 chloride, benzene sulfonyl chloride and the like, phenylacetonitrile as described by Schultz et al. or an aliphatic sulfonyl chloride such as methane (J. A. C. S. 69, 188-189, Jan. 1947). As pointed Sulfonyl chloride. out by these workers, however, when 2,2-diphen The reaction between propylene chlorohydrin y - 3 - methyl-4-dimethylamino - butyronitrile is and the aromatic sulfonyl chloride is ordinarily 25 prepared by this procedure, there is obtained, carried out in the presence of pyridine, preferably at the same time and mixed with this compound, at a temperature of approximately 0o C. Under...} the isomeric nitrile 2,2-diphenyl-4-methyl-4-di these conditions, the reaction is usually complete methylamino-butyronitrile. The latter nitrile after a reaction period of 1 to 3 days. The pyri isoner constitutes an unwanted by-product since dine hydrochloride, formed as a by-product of it cannot be converted to isoamidone. 30 this reaction, ordinarily precipitates arid is sepa Moreover, the preparation of isoamidone di rated from the reaction mixture by filtration. rectly from the mixture of isomeric nitriles has The filtrate is then mixed withi water and an or not proven feasible. In order to prepare iso ganic water-immiscible solvent such as ether, anidone, it has therefore previously been nec chloroform, benzene, toluene, xylene and the like. essary to isolate the desired 2,2-diphenyl-3-meth 35 The ether layer is separated and washed with an yl-4-dimethylamino-butyronitrile from the mix aqueous solution of a mineral acid such as hy ture and this has necessitated a complicated drochloric acid, hydrobromic acid, sulfuric acid, separation procedure which results in a consider and the like, and then with water. The ethereal able loss of the desired isomer. solution is dried and evaporated to dryness under 40 reduced pressure to produce, in the form of an It is now discovered that the desired 2,2-di oily residue, the corresponding 1-methyl-2-chloa phenyl-3-methyl - 4 - dimethylamino-butyroni trile can be prepared by a novel process which roethyl organic sulfonate, as for example 1-meth does not produce any of the unwanted isomeric yl-2-chloroethyl-p-toluenesulfonate, 1 - methyl nitrile. This improved method thus eliminates 2-chloroethyl-benzenesulfonate, 1-methyl-2- the loss due to formation of the by-product iso 45 chloroethyl-methane-sulfonate, and the like. iner and at the same time avoids the need for a This product is ordinarily purified by treatment complicated separation procedure with its at with aqueous pyridine to convert the residual or tendant losses of the desired isoner. ganic sulfonyl chloride to an acid. The resulting This novel process is conducted as follows: mixture is treated with an organic water-im propylene chlorohydrin (compound below) is 50 miscible solvent and aqueous hydrochloric acid reacted with an organic sulfonyl chloride (com and the layers are separated. The organic sol pound 2) to produce the corresponding 1-meth vent layer is washed first with an aqueous solu yl-2-chloroethyl-Sulfonate (compound 3). This tion of a mineral acid and then with water; compound is then treated with the reaction prod the organic layer is then further purified, if de luct of diphenyl acetonitrile and sodamide to pro 55 sired, by washing with an aqueous alkaline solti 2,671,798 s 4. tion such as aqueous sodium hydroxide, aqueous moiety thus forming the unwanted 2,2-diphenyl potassium hydroxide, aqueous ammonium hy 4- (organic-sulfonyl)-valeronitrile. The forma droxide, and the like, and again with Water. The tion of this compound, in other than Small solvent layer is then dried and evaporated to dry amounts, would make the reaction impractical. ness in vacuo to produce the desired 1-methyl-2- The 2,2-diphenyl-3-methyl-4-chloro - butyro chloroethyl organic sulfonate as a clear light yell nitrile is then reacted with substantially anhy low oil which is ready for use in the reaction drous dimethylamine. Small amounts of Water with diphenyl acetonitrile. are not harmful, but larger amounts result in The above procedure can be varied by using a heterogeneous mixture of reactants. It is a considerable excess of pyridine in the reaction O therefore preferred to conduct the reaction un between the organic sulfonyl chloride and propyl der substantially anhydrous conditions. It is ene chlorohydrin. Under these conditions, there ordinarily desired to employ an excess of di is an excess of pyridine present after the pyri methylamine in the reaction. Since dimethyl dine hydrochloride is removed by filtration. The amine is a gas at room temperature, it is con addition of water at this point followed by a venient to mix the reactants together at a ten standing period results in complete hydrolysis perature below about 7° C. The mixture of re of sulfonyl chloride. The step of purifying the actants is then heated in a pressure vessel to a first oily residue is eliminated since the 1-methyl temperature of approximately 100-150° C. Un 2-chloroethyl organic sulfonate formed at this der these conditions, the reaction is ordinarily stage is of satisfactory purity for employment in 20 complete in approximately 48 hours. the Subsequent reaction step. If desired, the reaction can be carried out in The 1-methyl-2-chloroethyl organic Sulfonate the presence of a solvent for the reactants, Such is treated with the reaction product of diphenyl as ethyl alcohol, and at a temperature of about acetonitrile and sodamide. The diphenylaceto 100-150° C. It has been found, however, that nitrile is mixed with an equivalent mola' Quan 25 the presence of an organic Solvent, such as eth tity of Sodamide and a liquid hydrocarbon, pref anol, tends to lower the yield. It is ordinarily erably a liquid having a boiling point of at least preferred, therefore, to carry out the reaction about 110° C., such as xylene, toluene, or liquid utilizing dimethylamine and 2,2-diphenyl-3- petrolatum. The resulting mixture is heated methyl-4-chloro-butyronitrile as the Sole con and stirred until at least about 95% of the theo 30 ponents, and to conduct the reaction at the retical amount of ammonia, has been liberated, higher temperature of 150° C. employing the which ordinarily requires between about 3 and 5 longer reaction period (48 hours), Since these hours. The reaction is ordinarily Carried out at conditions have been found to result in the Ob a temperature of about 105-110° C. under reflux tainment of a higher yield than that obtainable and in the presence of a nitrogen atmosphere. 35 When the reaction is carried out in the presence This reaction mixture is then cooled to be of a solvent. tween about 70 and 90° C. and the 1-methyl-2- A mixture of water and an organic water chloroethyl organic sulfonate is added thereto immiscible solvent such as ether, chloroform, rapidly, preferably keeping the temperature be benzene, toluene, xylene, and the like, is then low about 90° C. The resulting mixture is then 40 added to the reaction mixture and the Organic heated under reflux until the reaction is Sub solvent layer is extracted with an aqueous Solu stantially complete, which ordinarily requires tion of a mineral acid such as hydrobromic acid, about 14 to 18 hours. The reaction mixture is sulfuric acid, and the like. The aqueous acid then mixed with water, and the organic layer is extracts are then neutralized with an inorganic separated, washed With Water and dried. The base such as sodium hydroxide, potassium hy organic layer is evaporated to dryness to pro droxide, ammonium hydroxide and the like, and duce a crude product which may be used, if de the aqueous alkaline solution extracted with an sired, in the subsequent reaction with dimethyl organic Water-immiscible solvent.
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