Propyl-amine halides

The amines are a group of compounds with the general formula R-NHj, and all the common amines are hazardous. As a class the amines pose more than one hazard, being flammable, toxic, and, in some cases, corrosive. The amines are an analogous series of compounds and follow the naming pattern of the alkyl halides and the alcohols that is, the simplest amine is methyl amine, with the molecular formula of CH NHj. Methyl amine is a colorless gas with an ammonia-like odor and an ignition temperature of 806°F. It is a tissue irritant and toxic, and it is used as an intermediate in the manufacture of many chemicals. Ethyl amine is next in the series, followed by propyl amine, isopropyl amine, butyl amine and its isomers, and so on. 

Basic Character.—The alkyl amines then are analogous to alkyl halides, and we find a corresponding homologous series, e.g.j methyl amine, ethyl amine, propyl amine, etc. They are strongly basic compounds, in fact, they are of especial interest because they are more strongly basic than the ammonia from which they are derived. 

Notes on the preparation of secondary alkylarylamines. The preparation of -propyl-, ijopropyl- and -butyl-anilines can be conveniently carried out by heating the alkyl bromide with an excess (2-5-4mols) of aniline for 6-12 hours. The tendency for the alkyl halide to yield the corresponding tertiary amine is thus repressed and the product consists almost entirely of the secondary amine and the excess of primary amine combined with the hydrogen bromide liberated in the reaction. The separation of the primary and secondary amines is easily accomplished by the addition of an excess of per cent, zinc chloride solution aniline and its homologues form sparingly soluble additive compounds of the type B ZnCl whereas the alkylanilines do not react with sine chloride in the presence of water. The excess of primary amine can be readily recovered by decomposing the zincichloride with sodium hydroxide solution followed by steam distillation or solvent extraction. The yield of secondary amine is about 70 per cent, of the theoretical. 

Thirdly, this is where the staggering potential power of this recipe comes into focus. One can make, easily, pure mono-ethyl, mono-propyl, mono-isopropyl, mono-n-, s-, i- and t-NBT s. And using these directions, one can systematically react these mono s with every different alkyl halide. Thus, there suddenly becomes available a "this" times "that" squared possibilities of new tryptamines, every one easily made, every one potentially psychoactive, and almost every one totally unknown to the scientific literature. The oxalylamide process goes out to lunch when one considered the unlikelihood of finding N-s-butyl-N-i-butyl amine as a commercially available product. It is no longer required. Make IBSBT (how would you ever encode that product) by the simple treatment of one of these mono s with an appropriate alkyl halide, and clean up the mess with a dash of acetic anhydride. 

Although several methods have been reported, the synthesis of iV-monoalkylhydroxylamines from alkyl halides or sulfonates has remained difficult. Relating to this a new preparation of A -alkylhydroxyl-amines is based upon N-alkylation of isoxazole derivative (52). Besides 2-propyl iodide several primary alkyl halides have been described as the alkyladon agent in this procedure (equation 23). ... 

PROPYL CELLOSOLVE (Union Carbide) (2807-30-9) Forms explosive mixture with air (flash point 120°F/49°C cc). Reacts violently with oxidizers, permanganates, peroxides, ammonium persulfate, bromine dioxide, nitric acid, perchloric acid, sulfuric acid, and other strong acids. Incompatible with acyl halides, aliphatic amines, alkalis, boranes, isocyanates. 

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