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ChemicalBook CAS DataBase List Nicardipine
55985-32-5

Nicardipine synthesis

2synthesis methods
Nicardipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-methyl-2-[(methylphenylmethyl)- amino]ethyl ester 3,5-pirididincarboxylic acid (19.3.7), is synthesized in a manner analogous to the synthesis of nifedipine, the only difference being that in the Hantsch synthesis, two different β-dicarbonyl compounds are used simultaneously with o-nitrobenzaldehyde. During this, one of these in the enamine form of acetoacetic ester is simultaneously used as an amine component. A heterocyclization reaction is accomplished by reacting, the methyl ester of β-aminocrotonic acid with the 2-methyl-2-benzylaminoethyl ester of acetoacetic acid.

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: 100 percent / 1.) Et3N; 2.) H2O / tetrahydrofuran / 1.) 1 h; 2.) 0.5 h
2: 77 percent / 8 h / Heating

References:

Ohno;Komatsu;Mizukoshi;Ichihara;Nakamura;Morishima;Sumita [Chemical and Pharmaceutical Bulletin,1986,vol. 34,# 4,p. 1589 - 1606]

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