4-(4-Aminophenyl)morpholin-3-one
[CAS# 438056-69-0]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 4-(4-Aminophenyl)morpholin-3-one
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• CAS Registry Number: 438056-69-0
• EC Number: 610-147-8
• SMILES: C1COCC(=O)N1C2=CC=C(C=C2)N

Properties

• Density: 1.268

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H411
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-(4-Aminophenyl)morpholin-3-one is a chemical compound with the molecular formula C11H12N2O2, featuring a morpholine ring substituted with an amino group and a phenyl group. This compound is noteworthy for its applications in medicinal chemistry and organic synthesis.

The synthesis of 4-(4-aminophenyl)morpholin-3-one generally involves a multi-step process. Initially, morpholine is reacted with an appropriate aldehyde or ketone to form a substituted morpholinone. The key step involves the introduction of the 4-aminophenyl group, which is typically achieved through a nucleophilic substitution reaction or a coupling reaction. In some cases, the synthesis may start with a pre-functionalized morpholine derivative that is further modified to include the 4-aminophenyl group. The final product is purified using standard techniques such as recrystallization or chromatography.

4-(4-Aminophenyl)morpholin-3-one has found significant applications in the field of medicinal chemistry. Its structural features make it a valuable intermediate in the synthesis of various pharmaceuticals. The morpholine ring is known for its ability to form stable and versatile structures, which can be further modified to develop compounds with specific biological activities. The presence of the 4-aminophenyl group provides additional functionalization opportunities, making the compound useful in the design of targeted therapies.

One notable application of 4-(4-aminophenyl)morpholin-3-one is in the development of potential anti-cancer agents. Research has demonstrated that derivatives of this compound can exhibit significant cytotoxic activity against various cancer cell lines. The compound's ability to interact with specific biological targets or pathways may contribute to its potential as a therapeutic agent. Additionally, 4-(4-aminophenyl)morpholin-3-one has been explored for its role in designing inhibitors of enzymes involved in cancer progression, offering potential strategies for targeted cancer treatment.

Furthermore, the compound's versatility extends to its use in the synthesis of other bioactive molecules. For instance, modifications to the morpholine ring or the phenyl group can lead to the development of compounds with diverse pharmacological properties. This makes 4-(4-aminophenyl)morpholin-3-one a valuable scaffold in the drug discovery process, enabling researchers to explore a range of chemical modifications and their effects on biological activity.

In addition to its medicinal applications, 4-(4-aminophenyl)morpholin-3-one is also of interest in the field of organic synthesis. The compound can serve as a building block for the synthesis of more complex organic molecules. Its reactivity and functional groups make it a useful intermediate for constructing various organic structures, including those with potential applications in materials science or chemical catalysis.

Overall, 4-(4-aminophenyl)morpholin-3-one is a compound with significant potential in both medicinal chemistry and organic synthesis. Its role as an intermediate in the development of pharmaceutical agents and its utility in constructing diverse organic molecules highlight its importance in advancing drug discovery and chemical synthesis.

References

2015. Facile approach for the synthesis of rivaroxaban using alternate synthon: reaction, crystallization and isolation in single pot to achieve desired yield, quality and crystal form. Sustainable Chemical Processes, 3(1).
DOI: 10.1186/s40508-015-0036-3

2023. Continuous-Flow Synthesis, Characterization, Antimicrobial Activity, and Docking Studies of Urea Derivatives of 4-(4-Aminophenyl)-3-morpholinone. Russian Journal of General Chemistry, 93(5).
DOI: 10.1134/s1070363223050262