Patent GB-493865-A (GB)
Title: Improved manufacture of organic nitrogen compounds
Filed: 1937-04-15
Abstract: Nitrogenous organic products which are stated to yield solutions having capillary active and bactericidal properties are obtained by treating with halogenated alkylamines aromatic hydroxy compounds carrying at least one lipophile radicle as substituent. The resulting amines may be converted into (a) salts with acids such as carboxylic acids, sulphinic acids, sulphonic acids, acetic acid, hydrocyanic acid, thiocyanic acid, sulphuric acid, perchloric acid or phosphoric acid; (b) quaternary ammonium salts by means of alkylating or aralkylating agents; or (c) amino oxides.  The lipophile radicle comprises alkyl, aralkyl or cycloalkyl radicles containing at least five carbon atoms which may be interrupted by oxygen, sulphur or nitrogen atoms or be substituted by hydroxy, keto or carboxyl groups. In examples: (1) b -diethylaminoethylchloride or its hydrochloride is condensed in the presence of sodium in alcohol with p-sec.-dodecyl-o-cresol, p-sec.-hexyl-o-cresol, p-sec.-tetradecyl-o-cresol, p-sec.-hexadecyl-o-cresol, p-sec.-octadecyl-o-cresol, p-cyclohexyl - o - cresol, (3 - methyl - 4 - hydroxyphenyl)undecyl ketone, 1-hydroxy-3-methyl-4-chlor-6-sec.-dodecylbenzene, 5-sec.-dodecyl-o-hydroxydiphenylether, o - benzyl - p - chlorphenol, 1 - hydroxy - 2 - methoxy - 4 - chlor - 6 - sec. - dodecylbenzene, sec. - dodecyl - 1 - hydroxynaphthalene, 1 : 3-dihydroxy - 4 - chlor - 6 - sec.-hexylbenzene and with p-tert. butyl-o-sec.-dodecylphenol; (2) p - sec. - dodecyl - o - cresol is treated in the presence of sodium and alcohol, with N-b -chlorethyl-piperidine, (methyl-cyclohexylamino) - b  - chlorethanehydrochloride, g  - diethylamino - b  - hydroxy - a  - chlorpropanehydrochloride and b  - (b 1 - diethylaminoethoxyethylchloride hydrochloride.  Quarternary ammonium salts are in some cases formed from the products by treating with benzylchloride or menaphthylchloride.  Derivatives of phenanthrene, anthracene diphenyl, quinoline, carbazole and p benzimidazol may be used as the aromatic hydroxy compounds carrying a lipophile radicle and substituents such as allyl, benzyl, ester, ether and cyanogen groups may be present.  For the manufacture of aromatic hydroxy compounds carrying a lipophile radicle, aromatic hydroxy compounds may be condensed with pentamethylcarbinol, b -ethyl-butylalcohol, olein alcohol, geraniol, undecylene alcohol, oleic acid, erucic acid, linoleic acid, ricinoleic acid, pine oil, cracked petroleum, benzines obtained by the synthesis of olefines, hexylcyclohexanol, decahydronaphthols and halogenated aliphatic and cycloaliphatic compounds.  The following halogenated alkylamino compounds are specified: dimethyl(d  - chlor - n - pentyl)amine, a  - dimethylamino - b  - methyl - g  - chlorbutane, a  - diethylamino - b - brompentane, a  - diethylamino - b  - hydroxy - g  - chlorpropane, b  - (b 1 - diethylamino ethylmercapto)ethylchloride, b -(b 1-diethylamine ethoxy)ethylchloride, 11-diethylamino - n - undecyl chloride, 7-diethylamino - n - heptylchloride, 10 - N - piperidyl - n - decylchloride, ethyl - (b  - diethylaminoethyl) (b  - methyl - g  - chlorbutyl)amine, a  - dimethylamino - b  - methyl - g  - hydroxy - a - chlorbutane, 1 - dimethylamino - 2 - cyclohexylbromide, N - pyrrolidylethylchloride and N-methyl - 3 - chlormethyl - D  - 3 - tetrahydropyridine.  Specification 282,453, [Class 2 (iii)], is referred to.  N - methyl - 3 - chlormethyl - D  - 3 - tetrahydropyridine is prepared by treating N-methyl-D -3-tetrahydropyridine-3-aldehyde with sodium amalgam and chlorinating the resulting alcohol with thionylchloride.  Methylcyclohexylamino - b  - chlorethanehydrochloride is prepared by treating methylcyclohexyl amine with b -chlorethylalcohol and treating the resulting methylcyclohexylaminaethylalcohol with phosphoruspentachloride.  b  - (b 1 - diethylaminoethoxy)ethylchloride is prepared by treating diglycolchlorhydrin with diethylamine and converting the resulting alcohol into its chloride.