53220-41-0

Basic information

• Product Name: 4-(4-Chlorobenzoyl)piperidine
• Synonyms: METHANONE, (4-CHLOROPHENYL)-4-PIPERIDINYL-;(4-CHLORO-PHENYL)-PIPERIDIN-4-YL-METHANONE;4-(4-CHLOROBENZOYL)PIPERIDINE;4-(4-Cluorobenzoyl)piperidine;3-HYDROXY-2-PYRIDINEMETHYLFORMATE;4-[(4-chlorophenyl)carbonyl]piperidine
• CAS NO: 53220-41-0
• Molecular Formula: C₁₂H₁₄ClNO
• Molecular Weight: 223.7
• Mol File: 53220-41-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 60-63℃
• Boiling Point: 356.2 °C at 760 mmHg
• Flash Point: 169.2 °C
• Appearance: Yellow/Solid
• Density: 1.168 g/cm³
• Vapor Pressure: 2.96E-05mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-(4-Chlorobenzoyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Chlorobenzoyl)piperidine(53220-41-0)
• EPA Substance Registry System: 4-(4-Chlorobenzoyl)piperidine(53220-41-0)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 53220-41-0(Hazardous Substances Data)

Usage

Uses

It is used as pharmaceutical intermediate. The derivative of this compound, 2-amino-3-(4-chlorobenzoyl)-4-[4-(alkyl/aryl)piperazin-yl]thiophene are used as allosteric enhancers of the A1-adenosine receptor.

InChI:InChI=1/C12H14ClNO/c13-11-3-1-9(2-4-11)12(15)10-5-7-14-8-6-10/h1-4,10,14H,5-8H2

Upstream product

• 108-90-7 chlorobenzene 
• 498-94-2 isonipecotic acid 
• 25503-90-6 1-acetyl-piperidine-4-carboxylic acid 
• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 
• 59084-15-0 N-acetyl-4-(p-chlorobenzoyl)piperidine 

Downstream Products

• 389891-27-4 (S)4-[4-(4-chloro-benzoyl)-piperidin-1-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 38077-13-3 4-(p-Chloro-α-hydroxybenzyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine 

Relevant articles and documents

Synthesis of Novel Aryloxyethylamine Derivatives and Evaluation of Their in Vitro and in Vivo Neuroprotective Activities

A series of aryloxyethylamine derivatives were designed, synthesized and evaluated for their biological activity. Their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR and HR-ESI-MS. The preliminary screening of neuroprotection of compounds in vitro was detected by MTT, and the anti-ischemic activity in vivo was tested using bilateral common carotid artery occlusion in mice. Most of these compounds showed potential neuroprotective effects against the glutamate-induced cell death in differentiated rat pheochromocytoma cells (PC12 cells), especially for (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone, (4-bromophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, (4-chlorophenyl)(1-{2-[(naphthalen-2-yl)oxy]ethyl}piperidin-4-yl)methanone, (4-chlorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone and {1-[2-(4-bromophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, which exhibited potent protection of PC12 cells at three doses (0.1, 1.0, 10 μM). Compounds (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, (4-fluorophenyl){1-[2-(naphthalen-2-yloxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed the significant prolongation of the survival time of mice subjected to acute cerebral ischemia and decreased the mortality rate at all five doses tested (200, 100, 50, 25, 12.5 mg/kg) and had significant neuroprotective activity. In addition, (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed outstanding neuroprotection in vitro and in vivo. These compounds can be used as a promising neuroprotective agents for future development of new anti-ischemic stroke agents. Basic structure–activity relationships are also presented.

Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters

In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT 1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [(-)-15b, (-)-15j, (-)-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.