Development of a continuous flow synthesis of propranolol: tackling a competitive side reaction

    • Sonia De Angelis1, 2
    • Paolo Celestini3
    • Rosa Purgatorio1
    • Leonardo Degennaro1, 2
    • Gabriele Rebuzzini3
    • Renzo Luisi1, 2
    • Claudia Carlucci1, 2
    • 1Department of Pharmacy - Drug Sciences, University of Bari "A. Moro" Via E. Orabona 4, Bari, Italy
    • 2Flow Chemistry and Microreactor Technology FLAME-Lab, Bari, Italy
    • 3COSMA S.p.A, Ciserano Italy

    This work reports the preparation of propranolol according to a flow process. Propranolol has been prepared paying attention to tackle the formation of the by-product tertiary amine, resulting from an additional ring opening of the starting epoxide. Remarkably, the use of catalytic amount of water resulted beneficial for the yield and purity of the desired propranolol, and to substantially reducing the amount of tertiary amine byproduct. The high concentration of the solutions allowed for a productivity of several grams/h.

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