168828-81-7

Basic information

• Product Name: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE
• Synonyms: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE;N-CARBOBENZOXY-3-FLUORO-4-MORPHOLINYL-ANILINE;(3-Fluoro-4-morpholin-4-ylphenyl)carbamic acid benzyl ester;Benzyl (3-fluoro-4-Morpholinophenyl)carbaMate;CarbaMic acid, N-[3-fluoro-4-(4-Morpholinyl)phenyl]-, phenylMethyl ester;Linezolid Benzyl IMpurity;Benzyl 3-Fluoro-4-(4-Morpholinyl)phenyl)carbaMate;[3-Fluoro-4-(4-Morpholinyl)phenyl]carbaMic Acid PhenylMethyl Ester
• CAS NO: 168828-81-7
• Molecular Formula: C₁₈H₁₉FN₂O₃
• Molecular Weight: 330.35
• EINECS: 1806241-263-5
• Mol File: 168828-81-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 123.0 to 127.0 °C
• Boiling Point: 451.8 °C at 760 mmHg
• Flash Point: 227 °C
• Appearance: /
• Density: 1.284 g/cm³
• Vapor Pressure: 2.36E-08mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 12.74±0.70(Predicted)
• CAS DataBase Reference: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE(168828-81-7)
• EPA Substance Registry System: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE(168828-81-7)

Safety Data

• Hazardous Substances Data: 168828-81-7(Hazardous Substances Data)

Usage

Uses

[3-Fluoro-4-(4-morpholinyl)phenyl]carbamic Acid Phenylmethyl Ester is an intermediate in the synthesis of Linezolid Dimer (L466520), an impurity of the antibacterial agent Linezolid (L466500).

InChI:InChI=1/C18H19FN2O3/c19-16-12-15(6-7-17(16)21-8-10-23-11-9-21)20-18(22)24-13-14-4-2-1-3-5-14/h1-7,12H,8-11,13H2,(H,20,22)

Upstream product

• 369-34-6 3,4-difluoronitrobenzene 
• 2689-39-6 3-fluoro-4-(4-morpholinyl)nitrobenzene 
• 110-91-8 morpholine 
• 501-53-1 benzyl chloroformate 
• 100-00-5 4-chlorobenzonitrile 
• 350-31-2 1-chloro-2-fluoro-4-nitrobenzene 
• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 

Downstream Products

• 168828-90-8 (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine 
• 165800-03-3 linezolid 
• 198410-26-3 4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 168828-84-0 (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one 
• 174649-09-3 (R)-methyl methanesulfonate 
• 1236077-61-4 (S)-5-((benzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 565176-85-4 (S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholino phenyl)-isooxazol-2-one 
• 168828-82-8 (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol 
• 487040-99-3 (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidine carboxylic acid 
• 213262-99-8 (3-Fluoro-4-morpholin-4-yl-phenyl)-((R)-2-oxiranyl-ethyl)-carbamic acid benzyl ester 
• 224323-50-6 linezolid 

Relevant articles and documents

Linezolid preparation method and linezolid refining method

The invention provides a linezolid preparation method, which comprises: hydrogenation reduction, amino protection and reduction reaction. The invention further provides a linezolid refining method, which comprises: purifying, refining, crystal transformation, impurity removal and other processes. According to the present invention, the reaction of the linezolid synthesis process is simple, the reagent used in the reaction is safe and non-toxic, the reaction yield is high, and the purification process of the refining method is simple, and does not require complicated chromatographic purification; and the linezolid preparation method and the refining method are suitable for large-scale industrial production.

A process for the preparation of linezolid

The invention relates to a linezolid (1) preparation method. The method comprises the following steps: reacting a raw material 3,4-difluoronitrobenzene with morpholine, reducing, reacting with benzyl chloroformate to obtain N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline, carrying out a ring closure reaction of N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline and (S)-N-(2,3-epoxypropyl)phthalimide, ammonolyzing, and acetylating to obtain linezolid (1).

PROCESS FOR PREPARATION OF CRYSTALLINE FORM I OF LINEZOLID AND ITS COMPOSITIONS

The present invention relates to a process for the preparation of crystalline form I of linezolid, comprising providing a solution of linezolid in a solvent, crystallizing and recovering the solid of Linezolid in crystalline form I at elevated temperature. The present invention also relates to the use of crystalline form I of linezolid prepared by the method of the present invention for preparing pharmaceutical compositions.