A novel method for resolution of amlodipine

Gotrane, Dinkar M. ; Deshmukh, Rajendra D. ; Ranade, Prasad V. ; Sonawane, Swapnil P. ; Bhawal, Baburao M. ; Gharpure, Milind M. ; Gurjar, Mukund K. (2010) A novel method for resolution of amlodipine Organic Process Research & Development, 14 (3). pp. 640-643. ISSN 1083-6160

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Official URL: http://pubs.acs.org/doi/abs/10.1021/op900283z

Related URL: http://dx.doi.org/10.1021/op900283z


The present invention relates to an industrially feasible and cost-efficient process for the preparation of isomerically pure S-amlodipine besylate hemipentahydrate (1), a useful calcium antagonist inhibitor. Previous workers reported that R-amlodipine-tartrate was crystallized out preferentially from the reaction mixture when naturally occurring L-tartaric acid and racemic amlodipine base in DMSO are mixed. In order to crystallize S-amlodipine-tartrate, the use of unnatural D-tartaric acid as a resolving agent in DMSO was required. However, the cost of D-tartaric acid was not conducive to overall cost efficiency in the resolution protocol. Subsequent to the above observations, we have developed a novel resolving system in which amlodipine base with natural L-tartaric acid in DMF as a solvent gave preferentially the S-form of amlodipine tartrate directly from the reaction. The optimization of this approach by adjusting the water percentage in DMF ensured consistent purity of S-amlodipine (+99%) and satisfactory resolution efficiency.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:11392
Deposited On:09 Nov 2010 05:37
Last Modified:02 Jun 2011 09:36

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