3-FLUORO-4-MORPHOLIN-4-YL-PHENYLAMINE Chemical Properties

Melting point:

121-123°C

Boiling point:

364.9±42.0 °C(Predicted)

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

6.53±0.40(Predicted)

color 

Off-White to Brown

InChI

InChI=1S/C10H13FN2O/c11-9-7-8(12)1-2-10(9)13-3-5-14-6-4-13/h1-2,7H,3-6,12H2

InChIKey

FQGIBHQUVCGEAC-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(N2CCOCC2)C(F)=C1

CAS DataBase Reference

93246-53-8(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

3-FLUORO-4-MORPHOLIN-4-YL-PHENYLAMINE Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Intermediate in the synthesis of Linezolid (L466500).

Definition

ChEBI: 3-Fluoro-4-morpholinoaniline is a member of morpholines.

Synthesis

The general procedure for the synthesis of 3-fluoro-4-(4-morpholinyl)aniline from 3-fluoro-4-(4-morpholinyl)nitrobenzene was as follows: 4-(2-fluoro-4-nitrophenyl)morpholine D1 (42.6 g, 0.19 mol) was dissolved in ethanol (1.2 L), 10% Pd/C catalyst (4 g) was added, and hydrogenation was carried out at standard temperature and pressure (STP) for 18 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was evaporated under vacuum to afford the target product 3-fluoro-4-(4-morpholinyl)aniline (36.9 g, 100% yield) as a colorless solid. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.96 (4H, m), 3.55 (2H, br s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1H, m).

References

[1] Patent: WO2005/58317, 2005, A1. Location in patent: Page/Page column 35
[2] Patent: WO2005/58885, 2005, A2. Location in patent: Page/Page column 33
[3] Patent: WO2005/75461, 2005, A1. Location in patent: Page/Page column 100
[4] Patent: WO2006/2956, 2006, A1. Location in patent: Page/Page column 31
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4052 - 4066

3-FLUORO-4-MORPHOLIN-4-YL-PHENYLAMINE(93246-53-8)Related Product Information

• Linezolid
• 4-(2-FLUORO-4-NITRO-PHENYL)-MORPHOLINE
• (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate
• O-descarbonyl O-Acetyl Linezolid
• Linezolid Impurity 33
• Linezolid Impurity 56
• DeacetaMide Linezolid PhthaliMide
• Linezolid IMpurity D HCl
• Linezolid Related Impurity 1
• Desacetyl-N,O-descarbonyl Linezolid
• Linezolid Impurity 21
• Linezolid Diphthalimide
• Linezolid Impurity 37
• Linezolid Impurity 24
• Linezolid Impurity 25
• Linezolid Impurity 34
• Linezolid Impurity 57
• (R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone