Question

Devise at least three different methods to prepare N-methylbenzylamine $PhC{H}_{2}NHC{H}_3$from benzene, any one-carbon organic compounds, and any required reagents.

Short answer

Methods to prepare N-methylbenzineamine from benzene

Step-by-step solution

Introduction of an alkyl chain on the benzene ring

It is done by the electrophilic aromatic substitution on the benzene ring. An electrophile attacks one of the hydrogen atoms on the benzene ring to form a substituted benzene ring.

Introduction of the amine group in the alkyl chain

The carbon chain is attacked with a base to introduce a leaving group into the carbon chain. An amine group is introduced to the carbon chain by direct reaction with either of $N{H}_3$ or alkylic amine compound.

Methods to prepare N-methylbenzineamine from benzene

As many as five methods to prepare N-methylbenzineamine from benzene are shown hereunder.

Methods to prepare N-methylbenzineamine from benzene