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287930-73-8

287930-73-8 Structure

287930-73-8 Structure
IdentificationBack Directory
[Name]

4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE
[CAS]

287930-73-8
[Synonyms]

-2-hydroxymorphoL
Aprepitant Impurity 48
Fosaprepitant Impurity B
Fosaprepitant Impurity 23
4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE
2-Hydroxy-4-(phenylMethyl)-3-Morpholinone
3-Morpholinone,2-hydroxy-4-(phenylMethyl)-
Aprepitant intermediates,4-Benzyl-2-hydroxy-morpholin-3-one
[EINECS(EC#)]

811-794-0
[Molecular Formula]

C11H13NO3
[MDL Number]

MFCD07776435
[MOL File]

287930-73-8.mol
[Molecular Weight]

207.23
Chemical PropertiesBack Directory
[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 Rotation]

0.30°(C=0.01g/ml CHCL3)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
[HS Code ]

2934.99.4400
Hazard InformationBack Directory
[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]

Glyoxylic acid

298-12-4

N-Benzylethanolamine

104-63-2

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

287930-73-8

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
Spectrum DetailBack Directory
[Spectrum Detail]

4-BENZYL-2-HYDROXY-MORPHOLIN-3-ONE(287930-73-8)1HNMR
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