4-(4-NITROBENZYL)MORPHOLINE Chemical Properties

Melting point:

79.6-80 °C

Boiling point:

349.4±27.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

5.82±0.10(Predicted)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

36/37/39-26-22

HS Code 

2933399990

MSDS

• Language:English Provider:ACROS

4-(4-NITROBENZYL)MORPHOLINE Usage And Synthesis

Chemical Properties

yellow-orange to orange crystalline powder

Synthesis

General steps: 1. 4-Nitrobenzyl bromide (72.084 g) and dichloromethane (470 mL, dried over molecular sieves) were added to a reaction flask under argon protection and stirred until completely dissolved. 2. Anhydrous potassium carbonate (91.909 g) was added as a base. 3. The reaction mixture was cooled in an ice bath for 20 minutes. 4. Slowly add morpholine dropwise (completion of dropwise addition in about 30 minutes). 5. After completion of the dropwise addition, the ice bath was removed and the reaction mixture was stirred at room temperature overnight. 6. Upon completion of the reaction, the reaction was quenched by the addition of water (150 mL). 7. The pH of the reaction mixture was adjusted to 4-5 with 5% aqueous citric acid. 8. After standing and layering, the organic phase was separated and washed once with deionized water (260 mL). 9. The organic phase was dried with anhydrous magnesium sulfate for 30 minutes, followed by filtration. 10. The filtrate was concentrated and dried under reduced pressure by an oil pump to afford 4-(4-nitrobenzyl)morpholine (71.9 g, 97.16% yield).

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2975 - 2990
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 6, p. 771 - 775
[3] Patent: EP2824108, 2015, A1. Location in patent: Paragraph 0101
[4] Patent: US2015/166595, 2015, A1. Location in patent: Paragraph 0219
[5] Patent: CN106432235, 2017, A. Location in patent: Paragraph 0089; 0090

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