Aqueous-Mediated N-Alkylation of Amines

• Published in: European Journal of Organic Chemistry Vol. 2007; no. 8; pp. 1369 - 1377
• Main Authors: Singh, Chingakham B., Kavala, Veerababurao, Samal, Akshaya K., Patel, Bhisma K.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2007; WILEY‐VCH Verlag; Wiley
• Subjects: Alkylation; Amines; Aqueous media; Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Surfactants; Tertiary amines; tertiary amines; ALKALI-METAL SALTS; REM RESIN; SOLID-PHASE SYNTHESIS; TERTIARY-AMINES; CHEMOSELECTIVE ACYLATION; ORGANIC-REACTIONS; amines; ACID PROTEASE INHIBITORS; aqueous media; PALLADIUM-CATALYZED AMINATION; surfactants; COMBINATORIAL SYNTHESIS; alkylation; REDUCTIVE AMINATION
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200600937

Direct N‐alkylation of primary amines to secondary/tertiary amines and of secondary amines to tertiary amines has been achieved in excellent yields by employing alkyl, benzylic and allylic halides in the presence of NaHCO3 in an aqueous medium at an elevated temperature. Amines of differentstereoelectronic nature react with ease with different halides. The selective formation of secondary amines and the formation of three different substituted tertiary amines are some of the interesting features of this methodology. Reaction in an aqueous medium, operationally convenient conditions, excellent yields and innocuous byproducts, and the absence of transition‐metal catalysts, expensive bases, solid supports and the formation of undesired quaternary ammonium salts makes this method a green chemical process. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)