Embutramide is a potent sedative drug. It was developed as a general anesthetic agent, but was found to be too dangerous for assumed purpose. It was used in veterinary medicine for euthanasia of a range of different animals, mainly small animals kept as pets but also large farm animals.

In our studies of three-step synthesis of Embutramide we have selected Phase-Transfer conditions¹ for alkylation of 1 in a first step and for catalytic reduction of 2 using sodium borohydride, nickel or cobalt salts² (Figure 1). Contrary to well known method of synthesis of amine 3³, used reagents provided mild conditions of reduction process under atmospheric pressure. The optimization of alkylation process of 1 will be presented in this article. The best results were obtained when 60% solution of KOH as a base and TBAB as a catalyst were used. Under these conditions the excellent yield and purity of the product was obtained and the product can be used for the next step without any purification. In the second step nitrile 2 was reduced to amine 3 by excess sodium borohydride, cobalt (II) chloride or nickel (II) chloride, in methanol. The amine 3 of good yield and very good purity was obtained (impurities were significantly limited).

1       1. Barbasiewicz M., Marciniak K., Fedoryński M., Tetrahedron Lett., 2006, 47, 3871-3874. 2. Satoh T., Suzuku S., Tetrahedron Lett., 1969, 4555-4558.
3. Erhart G., Chem.Ber., 1964, 97, 74-76.
This work was supported by PFO VETOS FARMA, 58-260 Bielawa ul Dzierżoniowska 21

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