N-(4-Oxocyclohexyl)phthalimide Chemical Properties

Melting point:

142.0 to 146.0 °C

Boiling point:

410.0±38.0 °C(Predicted)

Density 

1.357

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

-2.27±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C14H13NO3/c16-10-7-5-9(6-8-10)15-13(17)11-3-1-2-4-12(11)14(15)18/h1-4,9H,5-8H2

InChIKey

PWUJQPNLEZZILN-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1C1CCC(=O)CC1

CAS DataBase Reference

104618-32-8

Safety Information

HS Code 

2925.19.4200

N-(4-Oxocyclohexyl)phthalimide Usage And Synthesis

Uses

N-(4-Oxocyclohexyl) Phthalimide is an impurity of Pramipexol (P700755), a dopamine-D2-receptor agonist used in the early treatment of Parkinson''s disease and restless legs syndrome.

Synthesis

Example 1: Synthesis of 4-(phthalimido)cyclohexanone 4-(Phthalimido)cyclohexanol (146 g) was mixed with ethyl acetate (1000 mL), followed by the addition of sodium bromide (8 g) and 2,2,6,6-tetramethylpiperidin-1-oxyl radical (TEMPO, 0.5 g). A 10% aqueous sodium hypochlorite solution (1000 mL) was added in batches and the pH of the reaction mixture was adjusted to 7-8 using sodium bicarbonate while maintaining the reaction temperature between 5 and 20 °C. Upon completion of the reaction, the aqueous layer was separated, and the organic layer was washed with saturated aqueous sodium chloride (400 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give a white solid product in 95% yield.

References

[1] Patent: WO2010/78250, 2010, A1. Location in patent: Page/Page column 12
[2] Patent: WO2006/3677, 2006, A1. Location in patent: Page/Page column 10; 16
[3] Patent: US2011/280808, 2011, A1. Location in patent: Page/Page column 62
[4] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
[5] Patent: US2003/100596, 2003, A1

N-(4-Oxocyclohexyl)phthalimide(104618-32-8)Related Product Information

• Cyclohexanone