Tertiary amines quatemisation

Massing described a synthesis of systematically modified cationic lipids by solid-phase chemistry starting with the immobihsation of (/f)-2,3-epoxy-1 -propanol on 4-methoxytrityl chloride resin [157], Reaction of the epoxide with distinct long-chained amines was followed by reductive animation and tertiary amine quatemisation (see Fig. lib). This interesting method allowed the solid-phase coupling of three different lipophUic moieties on an amino group and the synthesis... 

The most convenient way of a quat synthesis consists in the exhaustive methylation using primary or secondary fatty amines and methyl chloride to yield RN (CH3)3Cr (I) and R2N" (CH3)2Cr (II), respectively [101, 102], In order to enhance the quat yield the reaction is carried out in an aqueous or alcoholic solution of sodium carbonate at 60-95 °C. Tertiary amine quatemisation with benzyl chloride gives benzylalkyldimethylammonium, or "benzalkonium", chloride (III) ... 

The synthesis of TSOSs is analogous to non-functionalized ILs. Indeed, the same key steps can be applied depending on the nature of the cation and the anion. Quatemisation of tertiary amines, phosphines and sulfides with a functionalized alkyl halide affords the desired functionalized ammonium, phosphonium and sulfonium halides in usually... 

The reaction conditions can be selected to maximise the formation of imidazoline cationics quatemised derivatives of which have some importance as cationic fabric softeners [22c, 98, 99, 102]. Surface-active tertiary amines can be formed from alkyl chlorides, acyl chlorides or fatty esters as can be illustrated by the following reactions ... 

The oldest and most convenient synthesis of betaine-type amphiphiles is the quatemisation of higher tertiary amines with aqueous sodium chloroacetate at 70-90 °C [74, 111] ... 

Surface-active betaines can be synthesized also by quatemisation of long-chain tertiary amines with acrylic acid or P-propiolactone and from partially acylated dibasic amino acids and alkyl halides. 

In reactions that involve bond formation using the lone pair of electrons on the ring nitrogen, such as protonation and quatemisation, pyridines behave just like tertiary aliphatic or aromatic amines. When a pyridine reacts as a base or a nucleophile it forms a pyridinium , cation in which the aromatic sextet is retained and the nitrogen acquires a formal positive charge. 

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