- The effective direct resolution procedure for the chiral drug bevantolol hydrochloride
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The solubility of the chiral drug bevantolol hydrochloride 1 in water and the azeotropic mixture ethanol-water has been investigated. It was found that rac-1 meets the requirements of Meyerhoffer's rule, so it was possible to reduce the ternary diagram, describing the solubility of 1, to a pseudo binary form, which facilitates the analysis of crystallization processes caused by temperature changes. On this basis, the effective and robust resolution procedure of racemic bevantolol hydrochloride by a preferential crystallization approach has been realized successfully.
- Bredikhina, Zemfira A.,Antonovich, Olga A.,Zakharychev, Dmitry V.,Bredikhin, Alexander A.
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p. 397 - 403
(2016/05/19)
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- One more chiral drug prone to spontaneous resolution: Binary phase diagram, absolute configuration, and crystal packing of bevantolol hydrochloride
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Spontaneous resolution of cardioselective β1-adrenergic blocker bevantolol hydrochloride 1·HCl was established by IR spectroscopy, differential scanning calorimetry, and by single crystal X-ray analysis both for enantiopure and racemic samples.
- Bredikhina, Zemfira A.,Zakharychev, Dmitry V.,Gubaidullin, Aidar T.,Bredikhin, Alexander A.
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experimental part
p. 171 - 176
(2010/03/26)
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- Process for preparation of bevantolol hydrochloride
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Disclosed is a new process for preparing bevantolol hydrochloride suitable for industrial production in which bevantolol hydrochloride can be obtained in a high yield and HVA of an expensive material can be recovered. The process for the preparation of bevantolol hydrochloride comprises the steps of: causing 3-(m-tolyloxy)-1,2-epoxypropane (TOEP) to react with β-(3,4-dimethoxyphenyl)ethylamine (HVA) of excess mole per mole of said TOEP; dissolving the reaction mixture in a halogenated hydrocarbon to give a solution; mixing the solution with hydrochloric acid; separating an organic layer from the resulting mixture; and obtaining 1-[(3,4-dimethoxyphenethyl)amino]-3-(m-tolyloxy)-2-propanol hydrochloride from the organic layer.
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