Trimethylamine quaternary ammonium salts from

Girard s reagent T is carbohydrazidomethyltrimethylammonium chloride (I) and is prepared by the reaction of the quaternary ammonium salt formed from ethyl chloroacetate and trimethylamine with hydrazine hydrate in alco-hoUc solution ... 

Either the tertiary amine or the quaternary ammonium salt can be stored as a stable equivalent of the exo-methylene compound. In our first example, the Mannich base with dimethylamine is first methylated with methyl iodide and then added to the conjugate addition reaction. Elimination of trimethylamine, which escapes from the refluxing ethanol as a gas, reveals the exo-methylene ketone in which the methylene group is exo to a chain. Fast conjugate addition of the stabilized enolate of diethyl malonate produces the product. 

Pyrroles of this type, where X is halogen, alcohol, alkoxy or amine, and especially protonated alcohol or alkoxy, or quatemised amine, easily lose X, generating reactive electrophilic species. Thus ketones can be reduced to alkane, via the loss of oxygen from the initially formed alcohol (cf. 16.12), and quaternary ammonium salts, typified by 2-dimethylaminomethylpyrrole metho-salts, react with nucleophiles by loss of trimethylamine in an elimination/addition sequence of considerable synthetic utility. ... 

Definition Quaternary ammonium salt formed from the reaction of hydroxypropyl trimethylamine with hydrolyzed rice bran protein Formula [(CH3)3NCH2CHOHCH2R] Cr, where R rep. the hydrolyzed rice bran protein moiety Uses Antistat in cosmetics Hydroxypropyltrimonium hydrolyzed silk Definition Quaternary ammonium chloride formed from reaction of hydroxypropyl trimethylamine with hydrolyzed silk... 

Carboxylic acid methyl esters. A methanolic soln. of oleanolic acid containing phenolphthalein as indicator titrated with a soln. of tetramethylammonium hydroxide in the same solvent, which is then removed by distillation, and the residual tetramethylammonium salt heated under reduced pressure with distillation of the resulting trimethylamine -> methyl oleanolate. Y 83%. F. e. s. V. Prelog and M. Piantanida, H. 244, 56 (1936) by gas-diromatography s. A. S. Hyman, J. Chromatogr. 45, 132 (1969) ethers from quaternary ammonium hydroxides and acetates cf. J. MacGee and K. G. Allen, Steroids 16, 19 (1970). 

In view of the capacity for auto-quaternization shown by 2- and 4-halo-genopyridines, the ready reaction of 4-chloropyridine with pyridine or the formation of (97) from 2-bromopyridine and 2-bromomethylquinoline is not surprising. However, with other tertiary amines the situation is less clear. Thus, with trimethylamine in a sealed tube at 45°, 2-bromopyridine gives in 3 weeks a large amount of solid, containing some trimethyl-(2-pyridyl)ammonium bromide. 2-Chloropyridine reacted more slowly, 3-chloropyridine not at all, and 4-chloropyridine did not give the expected quaternary salt . 4-Chloropyridine did not react with triethylamine at 175°. 

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