4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE Chemical Properties

Melting point:

134.0 to 138.0 °C

Boiling point:

441.7±45.0 °C(Predicted)

Density 

1.292±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

11.00±0.20(Predicted)

color 

White to Off-White

optical activity

0.30°(C=0.01g/ml CHCL3)

Safety Information

HS Code 

2934.99.4400

4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE Usage And Synthesis

Uses

2-Hydroxy-4-(phenylmethyl)-3-morpholinone, is an intermediate used for the synthesis of NK1 Receptor Antagonist Aprepitant (A729800), used as as antiemetic drugs.

Synthesis

A 50% aqueous solution of glyoxalate (67 mL, 0.61 mol) and tetrahydrofuran (130 mL) were added to a 250 mL round bottom flask and heated to reflux. A solution of N-benzylethanolamine (41.5 g, 0.27 mol) in tetrahydrofuran (20 mL) was slowly added dropwise under reflux conditions. After completion of the reaction, the tetrahydrofuran solvent was removed by rotary evaporator. Water (170 mL) was added to the residue, stirred and cooled to room temperature, followed by continued stirring in an ice water bath for 30 min to promote crystallization. The precipitated solid was collected by filtration and washed with ice water. The resulting pale yellow solid was dried to afford the target product 4-benzyl-2-hydroxy-morpholin-3-one (compound of formula VII, 51.8 g, 91% yield) with a melting point of 132-136 °C.

References

[1] Patent: CN103030668, 2016, B. Location in patent: Paragraph 0031-0033
[2] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2129 - 2135

4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE(287930-73-8)Related Product Information

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