| Identification | Back Directory | [Name]
N-CBZ-HEXAHYDRO-1H-AZEPIN-4-ONE | [CAS]
83621-33-4 | [Synonyms]
N-CBZ-4-OXOAZEPANE
N-Cbz-azepan-4-one
N-Cbz Azepane-4-one
4-oxoazepane-1-carboxyL
N-CBZ-4-perhydroazepinone
N-CBZ-PERHYDROAZEPIN-4-ONE
AZEPAN-4-ONE, N-CBZ PROTECTED
N-CBZ-HEXAHYDRO-1H-AZEPIN-4-ONE
1-Cbz-hexahydro-4-oxo-1H-azepine
PERHYDROAZEPIN-4-ONE, N-CBZ PROTECTED
4-OXO-AZEPANE-1-CARBOXYLIC ACID BENZYL ESTER
N-CBZ-4-perhydroazepinone N-CBZ-perhydroazepin-4-one
1H-AZEPINE-1-CARBOXYLIC ACID, HEXAHYDRO-4-OXO-, PHENYLMETHYL ESTER | [Molecular Formula]
C14H17NO3 | [MDL Number]
MFCD03788442 | [MOL File]
83621-33-4.mol | [Molecular Weight]
247.29 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H412 | [Precautionary statements ]
P273 | [Hazard Codes ]
Xi | [Risk Statements ]
52 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
2914290090 |
| Hazard Information | Back Directory | [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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