1047659-01-7

Basic information

• Product Name: entacapone; piperidine salt
• Synonyms: entacapone; piperidine salt
• CAS NO: 1047659-01-7
• Molecular Weight: 390.439
• Mol File: 1047659-01-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: entacapone; piperidine salt(CAS DataBase Reference)
• NIST Chemistry Reference: entacapone; piperidine salt(1047659-01-7)
• EPA Substance Registry System: entacapone; piperidine salt(1047659-01-7)

Safety Data

• Hazardous Substances Data: 1047659-01-7(Hazardous Substances Data)

Upstream product

• 26391-06-0 2-cyano-N,N-diethylacetamide 
• 116313-85-0 3,4-dihydroxy-5-nitrobenzaldehyde 
• 110-89-4 piperidine 
• 130929-57-6 entacapone 
• 80547-69-9 3-hydroxy-4-methoxy-5-nitrobenzaldehyde 
• 145195-63-7 (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide 

Downstream Products

• 130929-57-6 entacapone 

Relevant articles and documents

A new synthesis of Entacapone and report on related studies

A new synthesis of the catechol-O-methyltransferase (COMT) inhibitor, entacapone (E-isomer) has been achieved under mild conditions by amine-mediated demethylation of the precursor 2-Cyano-3-(3- hydroxy-4-methoxy-5-nitrophenyl) prop-2-eneamide, wherein the methoxyl group adjacent to a nitro group gets demethylated under nucleophilic attack. Similar demethylation was achieved on ethyl 2-cyano-3-(3, 4-dimethoxy-5-nitrophenyl) prop-2-enoate, 2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethylprop-2-enamide, ethyl 2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl) prop-2-enoate and ethyl 2-cyano-3-(4-methoxy-3-nitrophenyl) prop-2-enoate. The scope of demethylation has been studied. Analogues of ethyl 2-cyano-3-(3, 4-dimethoxy-5-nitrophenyl) prop-2-enoate wherein a methoxyl group is not adjacent to a NO 2 group are unaffected and phenolic derivatives yield the amine salts. Entacapone has been converted to salts with organic bases. The crystal structure of the isomer of entacapone (Z-isomer), a significant human metabolite of E-isomer has been established. NMR methods for deriving E and Z geometry and other similar molecules have been successfully established, mainly by studying the proton coupled 13C spectra. Preliminary studies reveal in vitro activity for some compounds against tuberculosis (TB) and dengue. [Figure not available: see fulltext.]

PROCESS FOR PREPARING ENTACAPONE SUBSTANTIALLY FREE OF Z-ISOMER, SYNTHESIS INTERMEDIATES THEREOF AND A NEW CRYSTALLINE FORM

The present invention relates to a new process for preparing Entacapone substantially free of Z-isomer from 3, 4-dihydroxy-5-Nitrobenzaldehyde and N, N-Dimethylcyano acetamide, or directly from a mixture of (E) - and (Z) - isomers of Entacapone, by formation of organic or inorganic salts, specially piperidine and sodium ones. A new crystalline form G of Entacapone can be obtained from this method in a fast, efficient, and simple way and substantially free of Z-isomer. Another object of the invention is a pharmaceutical composition comprising it.