Process development of 4-[N-methyl-N-(tetrahydropyran-4-yl) aminomethyl] aniline dihydrochloride: A key intermediate for TAK-779, a small-molecule nonpeptide …

…, M Wakimasu, H Mitsudera, K Tomimatsu

Index: Hashimoto, Hideo; Ikemoto, Tomomi; Itoh, Tatsuya; Maruyama, Hideaki; Hanaoka, Tadashi; Wakimasu, Mitsuhiro; Mitsudera, Hiroyuki; Tomimatsu, Kiminori Organic Process Research and Development, 2002 , vol. 6, # 1 p. 70 - 73

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Citation Number: 12

Abstract

A new and efficient synthesis of 4-[N-methyl-N-(tetrahydropyran-4-yl) aminomethyl] aniline dihydrochloride, a key intermediate for the CCR5 antagonist TAK-779, is described. Reductive alkylation of methylamine with tetrahydro-4 H-pyran-4-one followed by alkylation of N-methyl-N-(tetrahydropyran-4-yl) amine with 4-nitrobenzylbromide and reduction of N-(4- nitrobenzyl)-N-(tetrahydropyran-4-yl) amine results in a 78% isolated yield from the ...