4-Methylpiperazine-1-carbonyl chloride monohydrochloride → Zopiclone

HRID 507804

Reaktionsgleichung

Reaktionsgleichung von HRID 507804
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:16]([OH:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[C:9]2=[O:18])=[N:6][CH:7]=1.Cl.Cl[C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)=[O:22]>C(N(CC)CC)C>[CH3:29][N:26]1[CH2:27][CH2:28][N:23]([C:21]([O:18][CH:9]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[C:16](=[O:17])[C:15]3[N:14]=[CH:13][CH:12]=[N:11][C:10]2=3)=[O:22])[CH2:24][CH2:25]1

Komponenten

4

Edukt 2

HCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 64519726-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one

Produkt 1

HCID 5735Zopiclone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

In another embodiment, the invention provides a process to recycle the (R)-zopiclone, which remains in solution as waste product. (R)-zopiclone is recovered from the solution by any known conventional methods, for example, by solvent distillation, evaporation, or precipitation by adding a non-polar solvent, etc. This is followed by neutralization with base, extraction using methylene chloride followed by removal of the solvent. The (R)-isomer isolated is subjected to acid hydrolysis using aqueous HCl, obtaining 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo-[3,4-b]pyrazine. The compound, 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo-[3,4-b]pyrazine, is reacted with 1-chlorocarbonyl-4-methylpiperazine hydrochloride in a suitable organic solvent in the presence of triethyl amine and N,N-dimethylamino pyridine to obtain zopiclone in high yields. The racemate thus obtained is further resolved to obtain eszopiclone by the above stated method.

Quellen und Nachweise

ORD-Eintrag
ord-d2f026dc95fe4e5e926d80d824a76b3f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786304B2

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