113 
of the type NR'R"R'"X. 
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 0 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 
