Editing Amine (section)

== Synthesis ==
<!-- This section is linked from [[Organic reaction]] -->

===From alcohols===
Industrially significant alkyl amines are prepared from ammonia by [[alkylation]] with alcohols:<ref name=Ullmann/>
:<chem>ROH + NH3 -> RNH2 + H2O</chem>

===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]].

===From alkenes===
Disubstituted alkenes react with HCN in the presence of strong acids to give formamides, which can be decarbonylated.  This method, the [[Ritter reaction]], is used industrially to produce tertiary amines such as [[tert-octylamine|''tert''-octylamine]].<ref name=Ullmann/>

Hydroamination of alkenes is also widely practiced.  The reaction is catalyzed by zeolite-based [[solid acid]]s.<ref name=Ullmann/>

===Reductive routes===
Via the process of [[hydrogenation]], unsaturated N-containing functional groups are reduced to amines using hydrogen in the presence of a nickel catalyst. Suitable groups include [[nitrile]]s, [[organic azide|azide]]s, [[imine]]s including [[oxime]]s, amides, and [[Nitro compound|nitro]]. In the case of nitriles, reactions are sensitive to acidic or alkaline conditions, which can cause hydrolysis of the {{chem2|\sCN}} group. [[Lithium aluminium hydride|{{chem2|LiAlH4}}]] is more commonly employed for the reduction of these same groups on the laboratory scale.

Many amines are produced from aldehydes and ketones via [[reductive amination]], which can either proceed catalytically or stoichiometrically.

[[Aniline]] ({{chem2|C6H5NH2}}) and its derivatives are prepared by reduction of the nitroaromatics. In industry, hydrogen is the preferred reductant, whereas, in the laboratory, tin and iron are often employed.

===Specialized methods===
Many methods exist for the preparation of amines, many of these methods being rather specialized.
{| class="wikitable sortable" style="background:white; float:center; margin:0 1em;"
|-
! style="width:200px;"|Reaction name !! Substrate !! class="unsortable" | Comment
|-
|valign=top| [[Staudinger reduction]]
|[[Organic azide]]
| This reaction also takes place with a reducing agent such as [[lithium aluminium hydride]].
|-
|valign=top| [[Schmidt reaction]]
|valign=top|[[Carboxylic acid]]
|
|-
|valign=top| [[Aza-Baylis–Hillman reaction]]
|valign=top|[[Imine]]
| Synthesis of allylic amines
|-
|valign=top| [[Birch reduction]]
|valign=top| [[Imine]]
| Useful for reactions that trap unstable imine intermediates, such as [[Grignard reaction]]s with [[nitrile]]s.<ref>{{cite journal|last1=Weiberth|first1=Franz J.|last2=Hall|first2=Stan S.|title=Tandem alkylation-reduction of nitriles. Synthesis of branched primary amines|journal=Journal of Organic Chemistry|date=1986|volume=51|issue=26|pages=5338–5341|doi=10.1021/jo00376a053}}</ref>
|-
|valign=top| [[Hofmann rearrangement|Hofmann degradation]]
|valign=top|[[Amide]]
| This reaction is valid for preparation of primary amines only. Gives good yields of primary amines uncontaminated with other amines.
|-
|valign=top| [[Hofmann elimination]]
|valign=top| [[Quaternary ammonium salt]]
|Upon treatment with strong base
|-
|valign=top| [[Leuckart reaction]]
|valign=top| [[Ketone]]s and [[aldehyde]]s
| [[Reductive amination]] with [[formic acid]] and [[ammonia]] via an [[imine]] intermediate
|-
|valign=top| [[Hofmann–Löffler reaction]]
|valign=top| [[Haloamine]]
|
|-
|valign=top| [[Eschweiler–Clarke reaction]]
|valign=top| Amine
| [[Reductive amination]] with [[formic acid]] and [[formaldehyde]] via an [[imine]] intermediate
|}