Process for the preparation of (S)-(+)-10,11-Dihydro-10-hydroxy-5H-dibenz (B,F) azepine-5-carboxamide
AssigneeFarchemia S.R.L.
InventorsMauro Panunzio, Eileen Campana, Sabatino Pulcini, Gabriele Breviglieri
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Abstract
(S)-(+)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxyamide is prepared starting from racemic 5-cyano-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine by phthaloylation, separation of the diastereomeric salts of the phthaloyl derivative with (S)-phenylethylamine, hydrolysis of the (S, S) salt to (S)-(+)-5-cyano-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine and hydrolysis of the nitrile group of the latter to amido group, by treatment with peroxy compounds in alkali medium.
Claims4
A process for the preparation of (S)-(+)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f,]azepine-5-carboxyamide of formula 2
- characterized in that the nitrile group of (S)-(+)-5-cyano-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine of formula 7
- is hydrolyzed with peroxy compounds in alkali medium.
As a novel compound, a compound selected from the group consisting of:
- 5-cyano-10,11-dihydro-10-(2-carboxy)benzoyloxy-5H-dibenz[b,f]azepine of formula 3 and the related enantiomers;
- S-1-phenylethylamine S,S and S,R salts with 5-cyano-10,11-dihydro-10-(2-carboxy)benzoyloxy-5H-dibenz[b,f]azepine, of formulae 4 and 5;
- (S)-(+)-5-cyano-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine of formula 7.
Dependencies are inferred from the claim text.