Mechanochemical Unlocking of Phthalimide Transamidation: A Path to N-Substituted Phthalamides

The Journal of Organic Chemistry, vol. 90, pp. 13854–13861

Abstract

The transamidation (aminolysis) of phthalimide with primary and secondary aliphatic amines is reported, where reactivity is induced by mechanical forces without the need for catalysts, acids, or thermal activation. The reaction proceeds at room temperature to afford N -substituted phthalamides as the major products. It is carried out in a mixer mill using stainless-steel jars and balls. The scope is demonstrated with more than 20 examples, achieving yields of up to 98%.

Authors 3

1. Camilo Morales-Manrique

   Universidad de Los Andes

   Affiliation as printed

   Laboratory of Organic Synthesis, Bio and Organocatalysis, Chemistry Department, Universidad de los Andes, Cra. 1 No. 18A-12 Q:305, Bogotá 111711, Colombia

2. Carsten Bolm corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen 52074, Germany

3. Diego A. Gamba-Sánchez corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University · Universidad de Los Andes

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen 52074, Germany

   Laboratory of Organic Synthesis, Bio and Organocatalysis, Chemistry Department, Universidad de los Andes, Cra. 1 No. 18A-12 Q:305, Bogotá 111711, Colombia