Synthesis of carvedilol via 1-(9H-carbazol-4-yloxy)-3-(N-(2-(2-methoxy phenoxy)ethyl)-N-(4-methoxybenzyl) amino) propan-2-ol

B.An; Kumar; Raman Vysabhattar; G.Ramadasu; K.Mukkanti; G.Madhusudhan

Organic Chemistry: An Indian Journal
ISSN (PRINT): 0974-7516

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Abstract

Synthesis of carvedilol via 1-(9H-carbazol-4-yloxy)-3-(N-(2-(2-methoxy phenoxy)ethyl)-N-(4-methoxybenzyl) amino) propan-2-ol

Author(s): B.Anand Kumar, Raman Vysabhattar, G.Ramadasu, K.Mukkanti, G.Madhusudhan

Synthesis of carvedilol is described to avoid the formation of bis impurity (disclosed inEUROPEANPHARMACOPOEIA6.0,Volume 2.0 as Impurity B) by choosing a simple 2-(2-methoxyphenoxy)-N-(4-methoxybenzyl) ethanamine to open the oxirane ring of 4-((oxiran-2-yl)methoxy)-9H-carbazole gave the tertiary amine, 1-(9H-carbazol-4-yloxy)-3-(N-(2-(2- methoxyphenoxy)ethyl)-N-(4-methoxybenzyl)amino) propan-2-ol. Removal of the N-p-methoxybenzyl (PMB) group in the tertiary amine is achieved easily and completely to get the targeted carvedilol with high purity.