3-(4-Morpholinyl)aniline Chemical Properties

Melting point:

118 °C

Boiling point:

0°C

Density 

1.149±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)

form 

Solid

pka

5.27±0.10(Predicted)

color 

Pale Brown to Brown

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

22-36/37/39-26

RIDADR 

UN2811

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

2934999090

3-(4-Morpholinyl)aniline Usage And Synthesis

Uses

3-Morpholin-4-ylaniline can be used to prevent and treat influenza.

Definition

ChEBI: 3-Morpholin-4-ylaniline is a member of morpholines.

Synthesis

To a solution of 4-(3-nitrophenyl)morpholine (43) (4.16 g, 20 mmol) in methanol (50 mL) cooled to 0 °C in an ice water bath was added 10% palladium/carbon catalyst (460 mg). The reaction mixture was stirred at room temperature and under hydrogen atmosphere (1 atm) for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration through diatomaceous earth (Celite?). The filtrate was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 3-(4-morpholinyl)aniline (3.39 g, 95.2%) as an orange solid. The product was analyzed by LC-MS showing m/z(ESP): 179 [M+H]? and retention time (R/T) of 1.69 min, which is sufficiently pure to be used in subsequent reactions without further purification.

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 26, p. 8261 - 8269
[2] Patent: US2006/199804, 2006, A1. Location in patent: Page/Page column 31
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 407 - 416
[4] Patent: WO2007/339, 2007, A1. Location in patent: Page/Page column 52
[5] Patent: WO2003/90912, 2003, A1. Location in patent: Page/Page column 76

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