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- Title
Acceleration of Anti-Markovnikov Hydroamination in the Synthesis of an Active Pharmaceutical Ingredient.
- Authors
Mitic, Aleksandar; Skovby, Tommy; Dam-Johansen, Kim; Gernaey, Krist V.
- Abstract
Slow chemical reactions are a big challenge in the modern pharmaceutical industry. Their accelerations together with the introduction of continuous manufacturing modes are major drivers for future development. One example reaction is hydroamination, a reaction between unsaturated hydrocarbons and amines. Such a reaction type is the main focus of this work. More precisely, the anti-Markovnikov hydroamination reaction between cis/trans 9H-thioxanthene-2-chloro-9(2-propenylidene)-(9CI) and 1-(2-hydroxyethyl)piperazine (HEP) is investigated in detail. It has been traditionally performed in toluene with a huge excess of HEP and reaction times of up to 24 h. Acceleration of the reaction from 24 down to 4 h is achieved by switching from batch operation mode in toluene to either solventfree batch mode or microwave-assisted hydroamination with tetrahydrofuran as a solvent.
- Subjects
MARKOVNIKOV'S rule; HYDROAMINATION; CHEMICAL synthesis; PIPERAZINE; TETRAHYDROFURAN; BATCH processing
- Publication
Chemical Engineering & Technology, 2016, Vol 39, Issue 10, p1821
- ISSN
0930-7516
- Publication type
Article
- DOI
10.1002/ceat.201500673