The reaction of phenylamine with halogenoalkanes

The reaction of phenylamine with halogenoalkanes This is another reaction of phenylamine as a nucleophile, and again there is no  essential difference between its reactions and those of aliphatic amines.
Taking bromoethane as a typical halogenoalkane, the reaction with phenylamine  happens in the same series of complicated steps as with any other amine. We'll just look at the first step. On heating, the bromoethane and phenylamine react to give a mixture of a salt of a  secondary amine and some free secondary amine. In this case, you would first get N-ethylphenylammonium bromide: . . . but this would instantly be followed by a reversible reaction in which some unreacted  phenylamine would take a hydrogen ion from the salt to give some free secondary amine: N-ethylphenylamine. The reaction wouldn't stop there. You will get further reactions to produce a tertiary amine  and its salt, and eventually a quaternary ammonium compound. If you want to explore this  further, refer to the last link just up the page, and trace the sequence of equations through  using phenylamine rather than ethylamine.