Abstract The preparation of quinine, quinidine, isomers and derivatives thereof from the correspondingly substituted 4-methyl-quinoline and 1-acyl(or 1-H)-3-vinyl(or lower alkyl)-4-piperidine acetic acid esters (or acetaldehyde) through alternative series of reaction steps which comprise, condensation, halogenation, deacylation, reduction, cyclization and hydroxylation, is described. Also described is the preparation of 1-acyl(or 1-H)-3vinyl-4-piperidineacetic acids and esters thereof and 1-acyl-3vinyl-4-piperidineacetaldehyde utilizing the corresponding 7acyldecahydro-2H-pyrido(3,4-d)azepin-2-one, prepared from 2-acyl1,3,4,7,8,8a-hexahydro-6(2H)-isoquinolone. The end products are useful as antimalarial and antiarrhythmic agents.
Epimers in accordance with claim 1, wherein R1 is methoxy; R2 is vinyl; R5 is methyl and m is 1, i.e., epimeric 6-methoxy-4-(3-(3(R)-vinyl-4(S)-piperidyl)-2 epsilon -acetoxypropyl)quinolines.
Claim 4
Dependent Claim
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Epimers in accordance with claim 1, wherein R1 is chloro; R2 is vinyl, R5 is methyl and m is 1, i.e., epimeric 7-chloro-4(3-(3(R)-vinyl-4(S)-piperidyl)-2 epsilon -acetoxypropyl)quinolines.
Claim 5
Dependent Claim
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Epimers in accordance with claim 1, wherein R1 is chloro; R2 is vinyl; R5 is methyl and m is 2, i.e., epimeric 6,8-dichloro-4-(3-(3(R)-vinyl-4(S)-piperidyl)-2 epsilon -acetoxypropyl) quinolines.