Editing Amine (section)

===From alkyl and aryl halides===
Unlike the reaction of amines with alcohols the reaction of amines and ammonia with alkyl halides is used for synthesis in the laboratory:
:<chem>RX + 2 R'NH2 -> RR'NH + [RR'NH2]X</chem>
In such reactions, which are more useful for alkyl iodides and bromides, the degree of alkylation is difficult to control such that one obtains mixtures of primary, secondary, and tertiary amines, as well as quaternary ammonium salts.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1= Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}</ref>

Selectivity can be improved via the [[Delépine reaction]], although this is rarely employed on an industrial scale.  Selectivity is also assured in the [[Gabriel synthesis]], which involves [[organohalide]] reacting with [[potassium phthalimide]].

Aryl halides are much less reactive toward amines and for that reason are more controllable.  A popular way to prepare aryl amines is the [[Buchwald-Hartwig reaction]].