3,3-Pentamethylene glutarimide Chemical Properties

Melting point:

84-89 °C(lit.)

Boiling point:

362.3±11.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

11.71±0.20(Predicted)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

1130-32-1(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

CM0120000

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

3,3-Pentamethylene glutarimide Usage And Synthesis

Chemical Properties

White Solid

Uses

Gabapentin intermediate.

Synthesis

To a 100 mL three-necked flask equipped with a thermometer, mechanical stirrer and reflux condenser were added 1,1-cyclohexanediacetic acid (10.0 g, 50 mmol) and formamide (4.5 g, 100 mmol). The reaction mixture was heated and the initial suspension was gradually transformed into a clarified colorless solution, the heating was continued and the reaction was stirred at 150-160 °C for 4 hours. The hot clarified reaction mixture was carefully poured into water (40 mL). The resulting colorless precipitate was collected, washed with water (10 mL) and subsequently dried under vacuum to afford 8.80 g (97% yield) of 3,3-cyclopentanediyl glutarimide as a colorless solid (99.9% purity by HPLC) with a melting point of 168-169 °C (literature value 169-170 °C).1H NMR (300 MHz, DMSO-d6) δ: 10.67 (broad peak, 1H), 2.42 (single peak, 4H), 1.30-1.41 (multiple peaks, 10H); 13C NMR (75 MHz, DMSO-d6) δ: 172.72, 42.50, 35.29, 32.45, 25.36, 20.97. Mass spectrometry (ESI-MS): calculated value (M+H)+ for C10H15NO2: 182.23, measured value: 182.21.

References

[1] Organic Preparations and Procedures International, 2013, vol. 45, # 6, p. 504 - 506

3,3-Pentamethylene glutarimide(1130-32-1)Related Product Information

• Cyclohexane
• Maleimide
• O-Phthalimide
• Succinimide
• Bismaleimide
• Glutarimide
• 2-CYCLOHEXYL-ETHYLAMINE HYDROCHLORIDE
• 4,4-dimethylpiperidine
• 3-AZASPIRO[5.5]UNDECANE
• 3-ETHYL-3-METHYLGLUTARIMIDE
• 2-Piperidone
• 3,3-DIMETHYLGLUTARIMIDE
• Polyamideimide
• DIALIFOS
• 3,3-Pentamethylene glutarimide (CDI) or 2-Azaspiro{4,5} decan-3-one,3,3-Pentamethylene glutarimide (CDI)
• 3,3-PENTAMETHYLENE-2-PYRROLIDINONE
• Cyclopentane
• 2-Pyrrolidinone