of the type NR'R"R 2 '"X. 



113 



Phenyldimethylbenzylammonium Iodide. This compound was 

 prepared both from dimethylaniline and benzyl iodide and from 

 methylbenzylaniline and methyl iodide. The latter method gave 



Fig. 5. 



'Fig. 6. 



the better yield and purer product. The compounds obtained 

 were found to be identical, even when the reaction was carried 

 out entirely at C C. An internal transformation, in which a 

 methyl and benzyl group are interchanged, must therefore have 

 taken place. The salt is readily soluble in water and hot alcohol, 

 somewhat less soluble in cold alcohol. It crystallises from alcohol 

 either in long or flat prisms of the prismatic system which melt to 

 a brown liquid at 163-4°. 



The corresponding dextro-camphorsulphonate was prepared by 

 heating the iodide, or the corresponding chloride prepared by 

 Michler and Gradmann {Ber. x. 2079), with the calculated 

 quantity of the silver salt of Reychler's acid and moist ethyl 

 acetate (Pope and Peachey's method, loc. cit). 



The white salt thus obtained is very soluble in water, alcohol 

 and chloroform, but sparingly soluble in benzene, ligroin, dry 

 ethyl acetate and acetone. It crystallises from a mixture of 

 chloroform and benzene and ligroin in plates of the oblique 

 system which melt at 189° with decomposition. 



Phenylmethyldibenzylammonium Iodide. A mixture of methyl- 

 benzylaniline and benzyl iodide sets in a few hours to a solid mass 

 of the above salt : the yield is nearly quantitative. After washing 

 with ether and crystallising from warm alcohol the salt is obtained 

 in colourless prisms of the prismatic system, which melt and 

 become brown at 134-5°. It is very sparingly soluble in water, a 

 characteristic property of dibenzyl compounds, but dissolves readily 

 in chloroform. 



The corresponding chloride was not formed from a mixture of 

 the tertiary amine and benzyl chloride after standing for months 

 or heating to 100° for some hours. It was therefore obtained by 

 digesting the iodide dissolved in warm alcohol with freshly pre- 

 pared silver chloride. The solution after filtering was evaporated 

 in a vacuum desiccator: a colourless crystalline mass was thus 



