4-hydroxy-2-Piperidinone Chemical Properties

Melting point:

165-168°C

Boiling point:

352.3±35.0 °C(Predicted)

Density 

1.199±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Methanol (Slightly, Sonicated)

pka

14.01±0.20(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C5H9NO2/c7-4-1-2-6-5(8)3-4/h4,7H,1-3H2,(H,6,8)

InChIKey

PRCAKTIAKXMBQF-UHFFFAOYSA-N

SMILES

N1CCC(O)CC1=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

4-hydroxy-2-Piperidinone Usage And Synthesis

Uses

4-Hydroxy-2-piperidinone is a synthetic intermediate in the synthesis of pharmaceutical goods.

Synthesis

Step 1) NaBH4 (1 g, 26.55 mmol) was slowly added to a solution of piperidine-2,4-dione (1 g, 8.8 mmol) in methanol (25 mL) at 0°C. The reaction mixture was stirred at room temperature overnight before the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol, 5:1, v/v) to afford 4-hydroxy-2-piperidone as a yellow solid (960 mg, 87% yield). m/z by LC-MS (ESI, positive ion mode): 138 [M + Na]+.

References

[1] Patent: WO2013/138210, 2013, A1. Location in patent: Paragraph 0258
[2] Patent: EP2947085, 2015, A1. Location in patent: Paragraph 0238; 0239; 0240

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