| Identification | Back Directory | [Name]
1-(4-Nitrophenyl)-2-piperidinone | [CAS]
38560-30-4 | [Synonyms]
1-(4-Nitrophenyl)-2-piperidone
1-(4-Nitrophenyl)-2-piperidinone
1-(4-Nitrophenyl)-2-piperidone >
2-Piperidinone, 1-(4-nitrophenyl)- | [Molecular Formula]
C11H12N2O3 | [MDL Number]
MFCD04037154 | [MOL File]
38560-30-4.mol | [Molecular Weight]
220.22 |
| Chemical Properties | Back Directory | [Melting point ]
97.0 to 101.0 °C | [Boiling point ]
480.9±28.0 °C(Predicted) | [density ]
1.295 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly),Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
-3.84±0.20(Predicted) | [color ]
Off-White to Yellow | [InChI]
InChI=1S/C11H12N2O3/c14-11-3-1-2-8-12(11)9-4-6-10(7-5-9)13(15)16/h4-7H,1-3,8H2 | [InChIKey]
VPCQXIGQMFWXII-UHFFFAOYSA-N | [SMILES]
N1(C2=CC=C([N+]([O-])=O)C=C2)CCCCC1=O |
| Hazard Information | Back Directory | [Uses]
1-(4-Nitrophenyl)-2-piperidinone is used in the synthesis of inhibitors of blood coagulation factor Xa. | [Synthesis]
5-Chloro-N-(4-nitrophenyl)pentanamide (72.3 g, 0.28 mol) was used as a raw material, which was mixed with K2CO3 and DMSO (360 mL) and the reaction was stirred at 80 °C for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into ice water (200 mL). The resulting precipitate was collected by filtration, washed with water and dried under reduced pressure to afford the target product 1-(4-nitrophenyl)-2-piperidone as a yellow powder (55.7 g, 89.6% yield). The melting point of the product was 96.4-98.3 °C; mass spectrum (ESI) m/z (%): 221.08 [M + H]+. | [References]
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5646 - 5661
[2] Patent: CN104650072, 2016, B. Location in patent: Paragraph 0122; 0125; 0129; 0130
[3] Patent: US2017/15663, 2017, A1. Location in patent: Paragraph 0141
[4] Synthetic Communications, 2013, vol. 43, # 1, p. 72 - 79
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 10, p. 2800 - 2810 |
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