38560-30-4

Basic information

• Product Name: 1-(4-Nitrophenyl)-2-piperidinone
• Synonyms: 1-(4-Nitrophenyl)-2-piperidinone;1-(4-Nitrophenyl)-2-piperidone
• CAS NO: 38560-30-4
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22458
• Mol File: 38560-30-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 97.0 to 101.0 °C
• Boiling Point: 480.921 °C at 760 mmHg
• Flash Point: 244.652 °C
• Appearance: /
• Density: 1.295
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly),Ethyl Acetate (Slightly)
• PKA: -3.84±0.20(Predicted)
• CAS DataBase Reference: 1-(4-Nitrophenyl)-2-piperidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Nitrophenyl)-2-piperidinone(38560-30-4)
• EPA Substance Registry System: 1-(4-Nitrophenyl)-2-piperidinone(38560-30-4)

Safety Data

• Hazardous Substances Data: 38560-30-4(Hazardous Substances Data)

Usage

Description

1-(4-Nitrophenyl)-2-piperidinone is an organic compound with the molecular formula C11H10N2O3. It is a derivative of piperidinone, featuring a nitrophenyl group attached to the first carbon and a phenyl ring at the second position. 1-(4-Nitrophenyl)-2-piperidinone is known for its potential applications in the pharmaceutical industry due to its unique structural properties.

Uses

1. Used in Pharmaceutical Industry:
1-(4-Nitrophenyl)-2-piperidinone is used as a key intermediate in the synthesis of inhibitors for blood coagulation factor Xa. These inhibitors play a crucial role in the prevention and treatment of various thrombotic disorders, such as deep vein thrombosis, pulmonary embolism, and acute coronary syndrome. 1-(4-Nitrophenyl)-2-piperidinone's structural characteristics allow for the development of potent and selective factor Xa inhibitors, which can help in reducing the risk of bleeding associated with anticoagulant therapy.
2. Used in Research and Development:
1-(4-Nitrophenyl)-2-piperidinone is also utilized in the research and development of new drugs targeting blood coagulation pathways. Its unique structure makes it a valuable tool for designing and optimizing novel therapeutic agents with improved efficacy, safety, and pharmacokinetic properties. Researchers can use this compound as a starting point for the synthesis of various analogs and derivatives, which can be further evaluated for their potential as anticoagulant drugs.

Upstream product

• 675-20-7 piperidin-2-one 
• 350-46-9 4-Fluoronitrobenzene 
• 4509-90-4 5-bromovaleroyl chloride 
• 100-01-6 4-nitro-aniline 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 1039914-85-6 5-chloro-N-(4-nitrophenyl)pentanamide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 91131-23-6 5-chloro-pentanoic acid phenylamide 
• 62-53-3 aniline 
• 4789-09-7 1-phenylpiperidin-2-one 
• 5134-88-3 sodium p-nitrobenzenesulphonic acid 

Downstream Products

• 503615-03-0 3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 881386-01-2 3,3-dichloro-1-(4-nitrophenyl)piperidine-2-one 
• 1267610-26-3 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one 
• 1643330-62-4 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide 
• 545445-44-1 5,6?dihydro?3?(4?morpholinyl)?1?[4?(2?oxo?1?piperidinyl)phenyl]?2(1H)?pyridone 
• 503614-91-3 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester 
• 536759-91-8 4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo- 1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester 
• 1423803-24-0 6-(4-aminophenyl)-1-(4-methoxyphenyl)-(4-methoxyphenyl)-7-carbonyl-1H-pyrazolo[3,4-c]-4,5,6,7-tetrahydropyridine-3-amide 
• 1437577-94-0 6-(4-(5-bromopentanamido)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 
• 1449510-64-8 6-(4-(5-chloropentanamido)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 
• 438056-68-9 1-(4-aminophenyl)piperidine-2-one 

Relevant articles and documents

Preparation method of apixaban intermediate suitable for industrial production

The invention discloses a synthesis method of an apixaban intermediate suitable for industrial production. The method comprises the following steps: carrying out phase-transfer catalytic amidation reaction on paranitroaniline and 5-chlorovaleryl chloride in an organic phase and water phase two-phase system under an inorganic weakly alkaline condition to obtain an APM01 solution, and adding a sodium hydroxide water solution, and cyclizing in a pot to obtain an APM02 solution; directly carrying out alpha-reactive hydrogen dichlorination on an APM02 organic solution and phosphorus pentachloride after simple acid pickling, liquid separation and drying to obtain an APM03 solution; carrying out condensation-elimination reaction on the APM03 solution and excessive morpholine after simple acid pickling and liquid separation, and carrying out simple crystallization and purification treatment to separate out an APM04 solid, and reducing the APM04 into APM05 by sodium sulfide; and carrying out amidation-cyclization two-step one-pot reaction on the APM05 and 5-chlorovaleryl chloride to prepare a key intermediate APM07. According to the method, the synthesis efficiency of the apixaban intermediate is improved, the reaction is mild, and dangerous NaH and other expensive reagents are not used, so that the production cost is saved, the operation is simple, and the method is suitable for industrial popularization.

Synthesizing method of intermediate of Apixaban

The invention belongs to the technical field of synthesizing of medicine intermediates, and particularly relates to a synthesizing method of an intermediate of Apixaban. The method includes the step of making 4-R-aniline and 5-chlorovaleryl chloride make contact for reaction in an inert solvent in the presence of amine quarter alkali to obtain the intermediate, namely 1-(4-R-aniline)piperidine-2-ketone, of Apixaban, wherein the reaction formula is shown as the formula I (the formula I is seen in the description). By means of the synthesizing method, the reaction efficiency and conversion rateof the intermediate of Apixaban are improved, there is no need to add tertiary amine organic base or use expensive NaH cyclization reagents, and production cost is saved.

Apixaban derivatives as well as preparation method and application thereof

The invention belongs to the technical field of medicines and discloses apixaban derivatives and analogues as well as a preparation method and application thereof. The structure of the compounds is shown as the following formula. Cheap and readily available paranitroaniline serves as an initial raw material. The preparation method comprises the following steps: performing amidation-cyclization, chlorination, condensation-elimination, cyclization-elimination, reduction, amidation-cyclization so as to obtain a key intermediate; and dehydrating, performing ammonolysis or chlorination, and condensing to synthesize the target compound. The method is simple in operation, convenient in after-treatment and high in yield. The in-vitro anti-coagulant activity of the target compound is investigated by determining the activated partial thromboplastin time (APTT) and thromboplastin time (PT). The EC2X(APTT) of result compounds APX-02, APX-15 and APX-16 is respectively 2.15mug/L, 3.65mug/L and 2.35mug/L, the EC2X(PT) of the result compounds is respectively 0.12mug/L, 3.57mug/L and 1.57mug/L, which are higher than the EC2X(APTT) value of 3.78mug/L and the EC2X(PT) value of 1.59mug/L of a positive control agent Apixaban. The compounds have high anti-coagulant activities. The EC2X(APTT) value of the rest compounds is between 5mug/L and 65mug/L, and the EC2X(PT) value is between 3mug/L and 18mug/L. The structural formula is as shown in the specification.