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Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines

Bruhaspathy Miriyala, Sukanta Bhattacharyya* and John S. Williamson

*Department of Chemistry, Argonaut Technologies, 1101 Chess Drive, Foster City, CA 94404, USA, Email:

B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron, 2004, 60, 1463-1471.

DOI: 10.1016/j.tet.2003.12.024


Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ reduction with sodium borohydride allows a highly chemoselective reductive mono-alkylation of ammonia. A simple workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes afforded the corresponding symmetrical secondary amines selectively.

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Selective Access to Secondary Amines by a Highly Controlled Reductive Mono-N-Alkylation of Primary Amines

H. J. Kumpaty, S. Bhattacharyya, E. W. Rehr, A. M. Gonzalez, Synthesis, 2003, 2206-2210.

Key Words

reductive amination, primary amines, benzylic amines, ammonia, sodium borohydride

ID: J72-Y2004-240