N-alkylation of anilines, carboxamides and several nitrogen heterocycles using CsF-celite/alkyl halides/CH3CN combination

It has been found that the N-alkylation of aniline, carboxamides and hetero cyclic compounds bearing an acidic hydrogen atom attached to nitrogen can b e accomplished with alkyl halides in acetonitrile and cesium fluoride-celit e employed as a solid base. In this manner, pyrrole, indole, pyrazole, imid azole, benzimidazole, carbazole, phthalimide, indazole, indoline, 2-pyrroli dinone, piperidine and 1,2,4-triazole can be successfully alkylated. The pr ocedure is convenient, efficient and generally gives rise to the N-alkylate d product exclusively. (C) 2001 Published by Elsevier Science Ltd.