84162-80-1

Basic information

• Product Name: 4-(2,4-DIFLUORO-BENZOYL)-PIPERIDINE-1-CARBALDEHYDE
• Synonyms: 4-(2,4-DIFLUORO-BENZOYL)-PIPERIDINE-1-CARBALDEHYDE;1-Formyl-4-(2,4-difluorobenzoyl)piperidine
• CAS NO: 84162-80-1
• Molecular Formula: C₁₃H₁₃F₂NO₂
• Molecular Weight: 253.24
• Mol File: 84162-80-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 64-66 °C
• Boiling Point: 402.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.336±0.06 g/cm3(Predicted)
• PKA: -1.70±0.40(Predicted)
• CAS DataBase Reference: 4-(2,4-DIFLUORO-BENZOYL)-PIPERIDINE-1-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-DIFLUORO-BENZOYL)-PIPERIDINE-1-CARBALDEHYDE(84162-80-1)
• EPA Substance Registry System: 4-(2,4-DIFLUORO-BENZOYL)-PIPERIDINE-1-CARBALDEHYDE(84162-80-1)

Safety Data

• Hazardous Substances Data: 84162-80-1(Hazardous Substances Data)

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 84163-43-9 1-formylisonipecotoyl chloride 
• 84163-42-8 1-Formylisonipecotic acid 
• 498-94-2 isonipecotic acid 

Downstream Products

• 84163-77-9 6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole 
• 150555-94-5 4-[4-Fluoro-2-(phenylmethylthio)benzoyl]-1-piperidinecarboxaldehyde 
• 514829-77-7 3-benzyloxy-2-(S)-[4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-1-propanol 
• 84163-13-3 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride 

Relevant articles and documents

Reformulating a Pharmacophore for 5-HT2A Serotonin Receptor Antagonists

Several pharmacophore models have been proposed for 5-HT2A serotonin receptor antagonists. These typically consist of two aromatic/hydrophobic moieties separated by a given distance from each other, and from a basic amine. Although specified distances might vary, the models are relatively similar in their general construction. Because our preliminary data indicated that two aromatic (hydrophobic) moieties might not be required for such action, we deconstructed the serotonin-dopamine antipsychotic agent risperidone (1) into four smaller structural fragments that were thoroughly examined in 5-HT2A receptor binding and functional (i.e., two-electrode voltage clamp (TEVC) and intracellular calcium release) assays. It was apparent that truncated risperidone analogues behaved as antagonists. In particular, 6-fluoro-3-(1-methylpiperidin-4-yl)benzisoxazole (4) displayed high affinity for 5-HT2A receptors (Ki of ca. 12 nM) relative to risperidone (Ki of ca. 5 nM) and behaved as a potent 5-HT2A serotonin receptor antagonist. These results suggest that multiple aromatic (hydrophobic) moieties are not essential for high-affinity 5-HT2A receptor binding and antagonist activity and that current pharmacophore models for such agents are very much in need of revision.

Process improvements for the preparation of kilo quantities of a series of isoindoline compounds

A series of isoindoline analogues with either an indazole (HMR 2934, HMR 2651) or benzisoxazole (HMR 2543) appendage were prepared for the proposed treatment of psychiatric disorders such as obsessive compulsive disorder and attention deficit disorder. The isoindoline compounds were prepared by reduction of the corresponding phthalimides with LiAlH4. One compound was not chiral, and the other two required an enantioselective synthesis. The key step for these optically active analogues involved the coupling by an SN2 process of either a piperazynyl intermediate or a piperdinyl intermediate with methyl 3-benzyloxy-2-trifluoromethansulfonatopropionate. The products for these two analogues had >98% ee. Process improvements led to the multi-kilogram syntheses of each of these compounds.

3-(4-Piperidyl)-1,2-benzisoxales

Novel 3-(4-piperidyl)-1,2-benzisoxazoles, intermediates and processes for the preparation thereof, and methods for alleviating pain utilizing compounds or compositions thereof are disclosed.