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Article

C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative

by
Zsolt Fülöp
1,
Péter Bana
2,
István Greiner
2 and
János Éles
2,*
1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
2
Gedeon Richter Plc, PO Box 27, 1475 Budapest, Hungary
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(7), 2040; https://doi.org/10.3390/molecules26072040
Submission received: 16 March 2021 / Revised: 29 March 2021 / Accepted: 29 March 2021 / Published: 2 April 2021
(This article belongs to the Special Issue Advances in Flow Chemistry)
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Abstract

A new, continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure consists of a DIBAL-H mediated selective ester reduction conducted in a novel, miniature alternating diameter reactor, followed by reductive amination using catalytic hydrogenation on 5% Pt/C. The connection of the optimized modules was accomplished using an at-line extraction to prevent precipitation of the aluminum salt byproducts.
Keywords: flow chemistry; C-N bond formation; consecutive reductions; cariprazine flow chemistry; C-N bond formation; consecutive reductions; cariprazine

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MDPI and ACS Style

Fülöp, Z.; Bana, P.; Greiner, I.; Éles, J. C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative. Molecules 2021, 26, 2040. https://doi.org/10.3390/molecules26072040

AMA Style

Fülöp Z, Bana P, Greiner I, Éles J. C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative. Molecules. 2021; 26(7):2040. https://doi.org/10.3390/molecules26072040

Chicago/Turabian Style

Fülöp, Zsolt, Péter Bana, István Greiner, and János Éles. 2021. "C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative" Molecules 26, no. 7: 2040. https://doi.org/10.3390/molecules26072040

APA Style

Fülöp, Z., Bana, P., Greiner, I., & Éles, J. (2021). C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative. Molecules, 26(7), 2040. https://doi.org/10.3390/molecules26072040

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