US EPA

7501711 

Journal Article 

Alkylation of Amines. A New Method for the Synthesis of Quaternary Ammonium Compounds from Primary and Secondary Amines 

Sommer, HZ; Jackson, LL 

1970 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

35 

5 

1558-1562 

English 

10.1021/jo00830a064 

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0000972842&doi=10.1021%2fjo00830a064&partnerID=40&md5=c464e19c0238ef41a02356d4481ae7fa
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Primary and secondary amines have been exhaustively alkylated to their quaternary stage in a one-step procedure. The observation that protonation of sterically hindered amines is only slightly affected by steric hindrance, whereas nucleophilicity as measured by the rate of alkylation is considerably decreased, has been synthetically utilized. An organic base of greater base strength than the reactant amines has been employed to bind the acid generated in alkylation reactions. Aniline and aniline derivatives with pKa values of 3.86-5.34 have been completely methylated in the presence of the stronger, but sterically hindered base, 2,6-lutidine (pKa = 6.77). The mild and homogeneous reaction conditions resulted in good yields with minimal laboratory manipulations and effort. As an example of the applicability of the method to amines that possess labile functions, the bisqua-ternary carbamate, 5-(dimethylcarbamoyloxy)-1,3-phenylenebis(trimethylammonium iodide), has been prepared from 3,5-diaminophenyl dimethylcarbamate in a one-step procedure. © 1970, American Chemical Society. All rights reserved.