N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE

Base Information

• Chemical Name: N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE
• CAS No.: 168828-81-7
• Molecular Formula: C₁₈H₁₉FN₂O₃
• Molecular Weight: 330.359
• Hs Code.: 2934999090
• European Community (EC) Number: 605-533-8
• DSSTox Substance ID: DTXSID50415463
• Nikkaji Number: J1.527.102G
• Wikidata: Q72475053
• ChEMBL ID: CHEMBL5005501
• Mol file: 168828-81-7.mol

Synonyms:Carbamicacid, [3-fluoro-4-(4-morpholinyl)phenyl]-, phenylmethyl ester (9CI);Benzyl3-fluoro-4-(4-morpholinyl)phenylcarbamate;N-Benzyloxycarbonyl-3-fluoro-4-morpholinoaniline;[3-Fluoro-4-(4-morpholinyl)phenyl]carbamic acid phenylmethyl ester;

Chemical Property of N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE

Chemical Property:

• Vapor Pressure: 2.36E-08mmHg at 25°C
• Melting Point: 123.0 to 127.0 °C
• Refractive Index: 1.605
• Boiling Point: 451.8 °C at 760 mmHg
• PKA: 12.74±0.70(Predicted)
• Flash Point: 227 °C
• PSA: 50.80000
• Density: 1.284 g/cm³
• LogP: 3.54900
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 330.13797063
• Heavy Atom Count: 24
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

[3-Fluoro-4-(4-morpholinyl)phenyl]carbamicAcidPhenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=C(C=C(C=C2)NC(=O)OCC3=CC=CC=C3)F
• 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).

Technology Process of N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE

There total 8 articles about N-BENZYLOXYCARBONYL-3-FLUORO-4-MORPHOLINOANILINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.1%

benzyl chloroformate (501-53-1,94274-21-2) + 3-fluoro-4-(morpholinyl)aniline (93246-53-8) → benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate (168828-81-7,1027135-00-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2013.01.052

Reference yield: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) → benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate (168828-81-7,1027135-00-7)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at -10 - 25 ℃; for 3h; under 608.041 - 912.061 Torr;

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate (168828-81-7,1027135-00-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-diisopropylethylamine

2: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran

3: NaHCO₃

With ammonium formate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(02)00043-4

upstream raw materials:

benzyl chloroformate

3-fluoro-4-(morpholinyl)aniline

3,4-difluoronitrobenzene

3-fluoro-4-(4-morpholinyl)nitrobenzene

Downstream raw materials:

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-5-((benzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

linezolid

(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholino phenyl)-isooxazol-2-one

Refernces

• 1、 Belousoff, Matthew J.,Venugopal, Hari,Wright, Alexander,Seoner, Samuel,Stuart, Isabella,Stubenrauch, Chris,Bamert, Rebecca S.,Lupton, David W.,Lithgow, Trevor. "cryoEM-Guided Development of Antibiotics for Drug-Resistant Bacteria". . p. 527 - 531. Retrieved 2019/02/19.
• 2、 -. "A kind of linezolid intermediate, preparation method thereof, and method for preparing and enduring zolamide". Paragraph 0040; 0041. . Retrieved 2017/04/04.