138680-08-7

Basic information

• Product Name: (R)-Zopiclone
• Synonyms: 1-Piperazinecarboxylic acid, 4-methyl-, (5R)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester (9CI);1-Piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester, (R)-;5H-Pyrrolo[3,4-b]pyrazine, 1-piperazinecarboxylic acid deriv.;Zopiclone R-Isomer CIV (10 mg) ((-)-(5R)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate);4-Methyl-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl ester-1-Piperazinecarboxylic acid;(R)-zolpiclone;(R)-4-Methyl-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl-1-piperazinecarboxylic Acid
• CAS NO: 138680-08-7
• Molecular Formula: C₁₇H₁₇ClN₆O₃
• Molecular Weight: 388.81
• Mol File: 138680-08-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 580.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.54±0.1 g/cm3(Predicted)
• PKA: 6.70±0.10(Predicted)
• CAS DataBase Reference: (R)-Zopiclone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Zopiclone(138680-08-7)
• EPA Substance Registry System: (R)-Zopiclone(138680-08-7)

Safety Data

• Hazardous Substances Data: 138680-08-7(Hazardous Substances Data)

Usage

Uses

(R)-Zopiclone is the (R)-enantiomer of Zopiclone (Z700500). (R)-Zopiclone is known to have sedative and anxiolytic effects and as well as effects towards locomotor activity reduction.

Upstream product

• 1020156-02-8 D(+)-O,O-dibenzoyl tartarate of zopiclone 
• 138729-47-2 eszopiclone 
• 915038-31-2 (R)-zopiclone L-malate 
• 43200-80-2 zopiclon 
• 144025-94-5 (R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt 
• 863393-46-8 (S)-(+)-6-(5-chloro-2-pyridinyl)-7-(4-methylpiperazin-1-yl-carbonyloxy)-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine-5-one D-(+)-malate 
• 1107971-11-8 (R)-zopiclone N-acetyl-L-aspartate 

Downstream Products

• 43200-80-2 zopiclon 
• 138729-47-2 eszopiclone 
• 43200-81-3 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one 

Relevant articles and documents

Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?

High-performance liquid chromatography (HPLC) and gas chromatography (GC) over chiral stationary phases (CSPs) represent the most popular and highly applicable technology in the field of chiral separation, but there are currently no CSPs that can be used for both liquid and gas chromatography simultaneously. We demonstrate here that two olefin-linked covalent organic frameworks (COFs) featuring chiral crown ether groups can be general CSPs for extensive separation not only in GC but also in normal-phase and reversed-phase HPLC. Both COFs have the same 2D layered porous structure but channels of different sizes and display high stability under different chemical environments including water, organic solvents, acids, and bases. Chiral crown ethers are periodically aligned within the COF channels, allowing for enantioselective recognition of guest molecules through intermolecular interactions. The COF-packed HPLC and GC columns show excellent complementarity and each affords high resolution, selectivity, and durability for the separation of a wide range of racemic compounds, including amino acids, esters, lactones, amides, alcohols, aldehydes, ketones, and drugs. The resolution performances are comparable to and the versatility is superior to those of the most widely used commercial chiral columns, showing promises for practical applications. This work thus advances COFs with high stability as potential universal CSPs for chromatography that are otherwise hard or impossible to produce.

Preparation of a β-cyclodextrin-based open-tubular capillary electrochromatography column and application for enantioseparations of ten basic drugs

An open-tubular capillary electrochromatography column was prepared by chemically immobilized β-cyclodextrin modified gold nanoparticles onto new surface with the pre-derivatization of (3-mercaptopropyl)-trimethoxysilane. The synthesized nanoparticles and the prepared column were characterized by transmission electron microscopy, scanning electron microscopy, infrared spectroscopy and ultraviolet visible spectroscopy. When the column was employed as the chiral stationary phase, no enantioselectivity was observed for ten model basic drugs. So β-cyclodextrin was added to the background electrolyte as chiral additive to expect a possible synergistic effect occurring and resulting in a better separation. Fortunately, significant improvement in enantioselectivity was obtained for ten pairs of drug enantiomers. Then, the effects of β-cyclodextrin concentration and background electrolyte pH on the chiral separation were investigated. With the developed separation mode, all the enantiomers (except for venlafaxine) were baseline separated in resolutions of 4.49, 1.68, 1.88, 1.57, 2.52, 2.33, 3.24, 1.63 and 3.90 for zopiclone, chlorphenamine maleate, brompheniramine maleate, dioxopromethazine hydrochloride, carvedilol, homatropine hydrobromide, homatropine methylbromide, venlafaxine, sibutramine hydrochloride and terbutaline sulfate, respectively. Further, the possible separation mechanism involved was discussed.

A process for racemisation of 6-(5-chloropyridin-2-yl)-7-(4-methyl-1-piperazinyl)carbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

The present invention provides a new process of recovering zopiclone from unwanted enantiomer by racemisation using aliphatic amines in amide solvents. The process of the present invention can give product in high yield with low amount of impurities and can be carried out on an industrial scale. The present invention provides also a method for resolving the enantiomers of zopiclone by means of chiral chromatography using stationary phase which comprises amylose tris (3,5-dimethylphenylcarbamate) immobilised on silica gel.