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United States Patent Office Patented Mar 2,976,280 United States Patent Office Patented Mar. 21, 1961 1. 2 phenol, cyclohexylphenol, benzoylphenol, nitrophenol, chlorophenol, 2- or 4-chloro-o-phenylphenol, ozozy 2,976,280 tetramethylbutylphenol, a,c,y,y-tetramethylbutylresorcin ol, thymol, carvacrol, 4-t-butylphenol, 6-t-butylphenol, 4 HEXAMETHYLENIMNEPHENOLS AND THER 5 t-butyl-o-cresol, 6-t-butyl-o-cresol, amylphenol, 6-t-amyl PREPARATION o-cresol, bis(p-hydroxyphenyl) dimethylmethane, 4,4'-iso Eric B. Hotelling, Westport, Conn., assignor to Consolida propylidenebis(o-cresol), 4,4'-methylenbis (o-cresol), sa tion Coal Company, Pittsburgh, Pa., a corporation of ligenin, guaiacol, catechol, hydroquinone, 8-hydroxy Pennsylvania quinoline, p-acetylaminophenol and pyrogallol. 0. The condensation can be carried out in an inert solvent No Drawing. Filed May 22, 1958, Ser. No. 736,979 such as water, alcohol, or dioxane. The formaldehyde 2 Claims. (C. 260-239) can be gaseous, aqueous, or parafolmaldehyde. - Depending on the procedure used, the compounds are obtainable in the form of either the base or the acid This invention relates to novel aminomethyl phenols 5 addition salt thereof. Hydrochloride, hydrobromide and and their preparation, and more particularly to phenols similar acid addition salts may be conveniently prepared containing a hexamethyleniminomethyl group. These from the Mannich base by well-known methods. Such compounds may be represented by the following formula salts may include, for example, those formed by reaction with the hydrohalogen acids, sulfuric acid, nitric acid, CH-CH-H, 20 phosphoric acid, thiocyanic acid, acetic acid, propionic R-CH-N acid, malonic acid, succinic acid, malic acid, methane C-C-CE sulfonic acid, lactic acid, tartaric acid and citric acid. where R is a phenolic aromatic nucleus. The compounds produced in accordance with this in Hexamethylenimine has been known and available for vention are of commercial importance as a means for more than half a century, and its reactions have been 25 introducing a methyl group into the aromatic nucleus of extensively studied. Non-phenolic aromatic compounds a phenolic compound. Thus the compound 6-t-butyl which contain a nuclearly attached hexamethylenimine 2,4-xylenol is a known and important article of com radical, such as the N-(p-aminophenyl)-hexamethyleni merce finding extensive application as an antioxidant in mines, are shown in U.S. Patent 2,612,500. The non gasoline, rubber, oils, plastics and the like. One method phenolic compounds shown are prepared by various 30 practiced commercially for obtaining this compound is methods, all of which differ from a Mannich condensa the direct butylation of 2,4-xylenol. However, inasmuch tion whereby the nitrogen atom is non-nuclearly attached as o-cresol is an important raw material, now available to the ring by means of a methylene linkage. in abundant quantity, a process suitable for commercial The Mannich reaction, which is well known, consists use for obtaining 6-t-butyl-2,4-xylenol starting with o in the condensation of a selected amine with formalde 35 cresol is of considerable importance. Conveniently, o hyde and a compound containing at least one hydrogen cresol may be reacted with isobutylene in the presence atom of pronounced reactivity. As pointed out by F. F. of sulfuric acid as catalyst to obtain 6-t-butyl-o-cresol. Blicke (Organic Reactions, vol. I, chap. 10, 1942) in his In accordance with this invention, the 6-t-butyl-o-cresol discussion of the scope of the Mannich reaction, cyclic may be condensed with equimolar amounts of formalde secondary amines differ considerably in their reactivity. 40 hyde and hexamethylenimine to form the phenolic Man Thus while morpholine undergoes the Mannich reaction nich base 4-(N-hexamethyleniminomethyl)-6-t-butyl-o- (see U.S. Patent No. 2,040,039), dicyclohexylamine and cresol. By hydrogenolysis of this compound, using a tetrahydroquinoline do not-see J. Am. Chem. Soc., vol. suitable catalyst such as a copper chromite or molyb 63, 1054 (1941) and vol. 58, 1570 (1936), respectively. denum sulfide catalyst, 6-t-butyl-2,4-xylenol is obtained, No Mannich reaction product of hexamethylenimine with 45 hexamethylenimine being regenerated. an aromatic compound is known. In particular, no In addition, the compounds of this invention possess hexamethyleniminomethyl phenolic derivatives have been important biological activity. Thus 4-(N-hexamethyl hitherto prepared. - eniminomethyl)-6-t-butyl-o-cresol and 4-(N-hexamethyl According to the present invention, these new com eniminomethyl)-2-methyl-6-t-amylphenol have been found pounds may be obtained by condensing any phenol having 50 effective as amebicides against Endamoeba histolytica at a free reactive nuclear hydrogen atom available for con a test dilution of 1:2,500. The test procedure followed densation with at least one molecular equivalent each of . , was substantially that described by Thompson et al. on hexamethylenimine and formaldehyde. p. 337, of Antibiotics and Chemotherapy (May 1956). Any nuclearly hydroxylated aromatic compound having Furthermore, the compound 6-(N-hexamethylenimino phenolic properties and a readily replaceable nuclear 55 methyl)-3,4-xylenol has been found to possess anti hydrogen atom can be used in the practice of this inven tubercular activity, completely inhibiting the growth of tion. These compounds, broadly designated as "phenols,” Mycobacterium tuberculosis at a serum broth concen can be monohydric or polyhydric, and may contain also tration of 10 micrograms per milliliter. other nuclear substituents such as aliphatic, aromatic, or The following examples illustrate this invention, but alicyclic hydrocarbon groups, halogen, alkoxy, nitro, 60 are not intended as limitations of the scope thereof. amino, acyl, acylamino, alkylol, nitrile, thiocyano or Example 1 other noninterfering radicals. Acidic groups such as : SOH interfere with the condensation and must first be OE neutralized. The term "phenols' as used broadly here CH-CH-H, in includes also hydroxylated polynuclear aromatic com 65 CH-N pounds such as the naphthols, hydroxyanthracenes, hy CH-CH-CH droxyquinolines, hydroxycarbazoles, and other nuclearly C hydroxylated aromatics. Typical common phenols which can be used in this CE condensation include phenol itself, o-, m-, and p-cresol, 70 6-(N-hexamethyleniminomethyl)-3,4-xylenol-Into a 2,3-, 2,4-, 2,6-, 3,4- and 3,5-xylenol, resorcinol, alpha 250-ml. Erlenmeyer flask was placed 12.2 g (0.1 mole) or beta-naphthol, o-, m-, and p-phenylphenol, benzyl . of 3,4-xylenol (Eastman) and about 100 ml, of absolute 2,976,280 3 A. ethanol. Then 9.9 g, of hexamethylenimine (0.1 mole) the aromatic nucleus of the phenol has more than one and 8.1 g of 37 percent aqueous formaldehyde solution reactive replaceable hydrogen atom, then more than one (0.1 mole) were added, and the flask was stoppered, hexamethyleniminomethyl group may be introduced. shaken, and allowed to stand overnight at room tempera One molecular equivalent each of formaldehyde and ture. Water was then added, and the product was sepa 5 hexamethylenimine is reacted with the phenol for each rated from the aqueous alcoholic solution as a heavy oil. such group to be introduced. The phenol used may be A sample of this oil was air-dried and solidified; it was either monocyclic or polycyclic. The replaceable hydro used to seed the remainder, which thereupon crystallized gen may be present either on the same ring or on linked at once. The solid base was filtered off, washed with rings, in a position ortho or para to the phenolic hy aqueous alcohol, and dried in vacuo; yield, 18.6 g. (80 droxyl group. Reactions of this type are illustrated in percent). Recrystallization from aqueous isopropyl al the following examples. cohol produced pure white crystals; M.P. 54-56 C. An infrared spectrum was obtained for characterization. Example 4 Analysis.--Calculated for C15H23NO: C, 77.20; H, CEIN(CH2)6 CH2N(CH2)6 9.93; N, 6.00. Found: C, 77.19; H, 10.20; N. 5.91. H The hydrochloride was precipitated from an ethereal Solution of the pure base by addition of dry hydrogen Ho-(D--(D-onCH chloride gas; M.P. 176-177° C. CE CH Analysis.-Calculated for C15H4NOCI: N, 5.19; Cl, 6,6'-bis(N-hexamethyleniminomethyl) - 4,4'-isopropyl 13.14. Found: N, 4.87; Cl, 13.14. 20 idene-bis(o-cresol)-A run was made in denatured al Example 2 cohol in accordance with the general procedure described in Example 1. The reactants were 12.8 g. (0.05 mole) 4,4'-isopropylidenebis(o-cresol), 9.9 g (0.10 mole) hexa methylenimine, and 8.1 g. (0.10 mole) 37 percent CH C(CH3)3 aqueous formaldehyde solution. After standing overnight, the heavy oil which formed CH-CH-CH was scratched to induce crystallization. Crystals were filtered off; the yield was 16.0 g. (67 percent based on phenol); M.P. (crude, dry) 144-153 C. (corr.). The CFI-CH-CH 30 compound was recrystallized from isopropyl alcohol and 4-(N - hexamethyleniminomethyl)-6-t-butyl-o-cresol.- dried in vacuo to constant weight; M.P. 160-163 C. Following essentially the same procedure described for (corr.). An infrared curve was obtained for character Example 1 and using denatured alcohol as solvent, 16.4 ization of the compound. g. (0.1 mole) 6-t-butyl-o-cresol, 9.9 g. (0.1 mole) hexa Analysis.-Calculated for C3H4N2O: C, 77.77; H, methylenimine, and 8.1 g. (0.1 mole) 37 percent aqueous 9.69; N, 5.85. Found: C, 77.57; H, 9.71; N, 5.48, 5.71. formaldehyde solution were reacted together. The yield, The dihydrochloride salt was prepared from an ethereal crude and dry, was 27.0 g. (98 percent); M.P. 91-96 C. solution of the base; 5.0 g. of base yielded 5.3 g (92.
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