Dimefline

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Dimefline
Dimefline.svg
Systematic (IUPAC) name
8-(dimethylaminomethyl)-7-methoxy-3-methyl-2-phenylchromen-4-one
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Registry Number 1165-48-6
ATC code R07AB08
PubChem CID: 3078
ChemSpider 2969
UNII 9WII5M0DU3 YesY
KEGG D07847 YesY
ChEMBL CHEMBL519364
Chemical data
Formula C20H21NO3
Molecular mass 323.38564 g/mol
 YesY (what is this?)  (verify)

Dimefline is a respiratory stimulant.

Synthesis[edit]

The Kostanecki acylation, which involves the esterification of ortho and acylphenol followed by aldol condensation of the resulting ketoester, provides a convenient entry to chromones. The subclass of 2-phenyl derivatives obtained by the use of benzoyl chloride is named flavones.

Dimefline synthesis:[1] GB 882537  P. Da Re, U.S. Patent 3,147,258 (1961, 1964 both to Recordati).

Reaction of o,p-dihydroxypropiophenone (1) with benzoyl chloride in the presence of sodium benzoate can be visualized as involving the initial formation of the ester (2). Internal condensation of the dicarbonyl derivative, which can proceed in only one direction, provides a new ring and results in a flavone (3). The remaining free phenolic group is then coverted to its methyl ether (4) by means of dimethyl sulfate. Reaction with formaldehyde in the presence of dry HCl (cf Blanc chloromethylation) serves to introduce a chloromethyl group (5). The displacement of chlorine by dimetylamine affords the respiratory stimulant dimefline (6).

References[edit]

  1. ^ Da Re et al., Arzneim.-Forsch. 10, 800 (1960).