N-CBZ-HEXAHYDRO-1H-AZEPIN-4-ONE Chemical Properties

Boiling point:

398.2±42.0 °C(Predicted)

Density 

1.177±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.55±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C14H17NO3/c16-13-7-4-9-15(10-8-13)14(17)18-11-12-5-2-1-3-6-12/h1-3,5-6H,4,7-11H2

InChIKey

ORJQXZSDLARZBC-UHFFFAOYSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCCC(=O)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

52

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2914290090

N-CBZ-HEXAHYDRO-1H-AZEPIN-4-ONE Usage And Synthesis

Synthesis

General procedure for the synthesis of N-CBZ-4-azepinone from ethyl 1-Cbz-5-oxoazepane-4-carboxylate: an aqueous solution of potassium hydroxide (24.6 g, 375 mmol) (400 mL) was added to an ethanolic solution of 5-benzyl 4-ethyl-5-oxo-1,4-azepanedicarboxylate (40.0 g, 125 mmol) (400 mL). The reaction mixture was heated to reflux for 2.5 hours. After completion of the reaction, it was cooled to room temperature and ethanol was removed by distillation under reduced pressure. Subsequently, the reaction mixture was diluted with 200 mL of brine and 300 mL of ethyl acetate. The organic and aqueous layers were separated and the aqueous phase was further extracted with ethyl acetate (2 x 100 mL). All organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange colored oil. Purification by fast column chromatography (silica gel, 40% ethyl acetate/hexane as eluent) gave a clarified colorless oily product (22.6 g, 73% yield). The structure of the product was analyzed by 1H NMR (CDCl3, δ: 7.31-7.30, 5.12, 3.65-3.63, 2.68-2.60, 1.81-1.78) and IR (liquid, cm-1: 1698, 1475, 1454, 1442, 1423, 1331, 1320, 1295, 1270, 1241, 1191 , 1165, 1091, 900, 699) confirmed.

References

[1] Patent: EP1173440, 2004, B1. Location in patent: Page 11
[2] Patent: EP1173440, A1. Location in patent: Page 11
[2] Patent: , 2002, . Location in patent: Page 11
[4] Patent: WO2008/39420, 2008, A2. Location in patent: Page/Page column 32
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 918 - 921

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