ChemicalBook CAS DataBase List 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

4-(4-AMINOPHENYL)MORPHOLIN-3-ONE synthesis

6synthesis methods

Product Name:4-(4-AMINOPHENYL)MORPHOLIN-3-ONE
CAS Number:438056-69-0
Molecular formula:C10H12N2O2
Molecular Weight:192.21

2-anilinoethanol (11) was condensed with ethyl chloroacetate in the presence of potassium tert-butoxide in tetrahydrofuran to afford the required phenylmorpholinone (12). Nitration of the intermediate morpholinone (12) in a solution of concentrated sulphuric acid with nitric acid below room temperature provided after recrystallization the para-product (13) in > 99.5% HPLC purity. The mother liquor was enriched predominantly with unwanted ortho - and meta-isomers together with depleted para-product. By subsequent hydrogenation of the nitro group in 13 with palladium on charcoal in methanol the 4-(4-Aminophenyl)morpholin-3-one (14) was obtained.
synthesis of 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

synthesis of 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

[1] W. MEDERSKI Markus W P Wendel. Practical and efficient processes for the preparation of 4-(4-aminophenyl)morpholin-3-ones on a larger scale: precursor of factor Xa inhibitors[J]. Heterocycles, 2007, 74 1: 437-445. DOI:10.3987/COM-07-S(W)22.

446292-04-2 Synthesis

446292-04-2
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438056-69-0
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Yield:438056-69-0 97.8%

Reaction Conditions:

with Pd/C;hydrogen in ethanol at 60; under 3000.3 Torr; for 3 h;Autoclave;

Steps:

4 Example 4:Preparation of 4-(4-aminophenyl)-3-morpholinone

1.57 g of 4-(4-aminophenyl)-3-morpholinone was added to the autoclave,An additional 0.37 g of palladium on carbon was added followed by 20 mL of absolute ethanol.After replacing the air in the vessel with hydrogen for three times, the oil bath is heated under hydrogen conditions.The mid-term hydrogen pressure is 0.4 MPa, the oil bath temperature is 60 ° C, and the stirring reaction is 3 h.The target product rivaroxaban intermediate 4-(4-aminophenyl)-3-morpholinone was obtained.After completion of the reaction, palladium carbon was removed by suction filtration, and the filtrate was concentrated under reduced pressure.Recrystallization from ethanol gives 4-(4-aminophenyl)-3-morpholinone,The yield was 97.8%.

References:

CN104788444,2018,B Location in patent:Paragraph 0041; 0042; 0043; 0044

109-11-5 Synthesis