78471-44-0

Basic information

• Product Name: 1-(4-CHLOROBENZYL)PIPERIDIN-4-AMINE TRIFLUOROACETATE
• Synonyms: 1-(4-Chlorobenzyl)-4-aminopiperidine;1-(4-Chlorobenzyl)-4-piperidinamine;1-(4-Chlorobenzyl)piperidin-4-ylamine
• CAS NO: 78471-44-0
• Molecular Formula: C₁₂H₁₇ClN₂
• Molecular Weight: 224.7298
• Mol File: 78471-44-0.mol

Chemical Properties

• Boiling Point: 311.6 °C at 760 mmHg
• Flash Point: 142.2 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0.000559mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 1-(4-CHLOROBENZYL)PIPERIDIN-4-AMINE TRIFLUOROACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLOROBENZYL)PIPERIDIN-4-AMINE TRIFLUOROACETATE(78471-44-0)
• EPA Substance Registry System: 1-(4-CHLOROBENZYL)PIPERIDIN-4-AMINE TRIFLUOROACETATE(78471-44-0)

Safety Data

• Hazardous Substances Data: 78471-44-0(Hazardous Substances Data)

Usage

Chemical structure

The compound consists of a piperidine ring with an amine group and a 4-chlorobenzyl group attached to it.

Counter-ion

The trifluoroacetate ion is the counter-ion, which is often used to increase the solubility and stability of the compound.

Pharmaceutical research

It is commonly used as a building block for the synthesis of various drugs and bioactive compounds.

Therapeutic potential

The compound has been studied for its potential as a therapeutic agent in the treatment of neurological disorders and as an analgesic.

Salt form preference

The trifluoroacetate salt form of the compound is often preferred due to its enhanced properties for drug development and formulation.

Solubility

The trifluoroacetate salt form improves the solubility of the compound, which is important for drug development and formulation.

Stability

The trifluoroacetate salt form also enhances the stability of the compound, making it more suitable for pharmaceutical applications.

Molecular weight

The molecular weight of the compound without the trifluoroacetate counter-ion is approximately 213.7 g/mol.

Appearance

The compound is typically a solid, with the appearance of a white or off-white powder or crystalline solid.

InChI:InChI=1/C12H17ClN2/c13-11-3-1-10(2-4-11)9-15-7-5-12(14)6-8-15/h1-4,12H,5-9,14H2

Upstream product

• 50541-93-0 4-amino-1-benzylpiperidine 
• 73889-19-7 tert-butyl (1-benzylpiperidin-4-yl)carbamate 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 1286275-72-6 tert-butyl 1-(4-chlorobenzyl)piperidin-4-ylcarbamate 
• 1052528-90-1 4-amino-1-(4-chloro-benzyl)-pyridinium chloride 
• 241495-43-2 4-carboxamide-1-(4-chlorobenzyl)piperidine 
• 68726-76-1 1-(p-chlorobenzyl)-4-piperidone oxime 

Downstream Products

• 548797-97-3 N-{2-[((2S)-3-{[1-(4-chlorobenzyl)piperidin-4-yl]amino}-2-hydroxy-2-methylpropyl)oxy]-4-hydroxyphenyl}acetamide 
• 1313481-22-9 N-(1-(4-chlorobenzyl)piperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine 
• 1033951-50-6 4-{5-bromo-2-[1-(4-chloro-benzyl)-piperidin-4-ylamino]-pyrimidin-4-yloxy}-3,5-dimethyl-benzonitrile 
• 936328-21-1 methyl (2E)-3-{2-[((2S)-3-{[1-(4-chlorobenzyl)piperidin-4-yl]amino}-2-hydroxy-2-methylpropyl)oxy]-5-fluorophenyl}acrylate 

Relevant articles and documents

Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase

In recent years, ALR2 (aldose reductase) inhibitors have attracted attention for their effective ability to reduce the progression of diabetes-associated cataracts. Therefore, in the present article, we intended to develop novel thiazole-sulfonamide hybrids as a potent inhibitor of ALR2. These molecules significantly inhibited the ALR2 level in the rat lenses homogenate, where the most potent compound 7b showed activity comparable to sorbinil as standard. In Wistar rats, compound 7b improved the insulin level and body weight of the experimental animal together with a reduction in the glucose output. Compound 7b showed a significant reduction in the expression of ALR2 in rat lenses in western blot analysis.

Substituted 2-thioxothiazolidin-4-one derivatives showed protective effects against diabetic cataract via inhibition of aldose reductase

In an effort to develop a new class of potent aldose reductase inhibitors against diabetic cataracts, a series of novel 2-thioxothiazolidine-4-one derivatives was synthesized in excellent yields via a facile synthetic route. These compounds were tested against aldehyde (ALR1) and aldose reductase (ALR2) enzymes, where they showed considerable inhibitory activity. Among the tested derivatives, compound 6e showed selective and excellent inhibition of ALR2 over ALR1. The experimental diabetes was induced by the intraperitoneal administration of streptozotocin in male Wistar rats. Compound 6e showed positive modulation of body weight, blood glucose, and blood insulin levels in diabetic rats. Compound 6e also showed ALR2 inhibition as evidenced by Western blot analysis in lens homogenates of Wistar rats having cataract. The docking study of 6e was also performed inside the active site of ALR2 to enumerate the key contacts for inhibitory activity.

Piperidinyl Ureas Chemically Control Defective in Cullin Neddylation 1 (DCN1)-Mediated Cullin Neddylation

We previously discovered and validated a class of piperidinyl ureas that regulate defective in cullin neddylation 1 (DCN1)-dependent neddylation of cullins. Here, we report preliminary structure-activity relationship studies aimed at advancing our high-throughput screen hit into a tractable tool compound for dissecting the effects of acute DCN1-UBE2M inhibition on the NEDD8/cullin pathway. Structure-enabled optimization led to a 100-fold increase in biochemical potency and modestly increased solubility and permeability as compared to our initial hit. The optimized compounds inhibit the DCN1-UBE2M protein-protein interaction in our TR-FRET binding assay and inhibit cullin neddylation in our pulse-chase NEDD8 transfer assay. The optimized compounds bind to DCN1 and selectively reduce steady-state levels of neddylated CUL1 and CUL3 in a squamous cell carcinoma cell line. Ultimately, we anticipate that these studies will identify early lead compounds for clinical development for the treatment of lung squamous cell carcinomas and other cancers.

Design and development of a novel chalcone derivative as an anticholinesterase inhibitor for possible treatment of dementia

Background: Cognitive decline (e.g., memory loss), which mainly occurs in the elderly, is termed dementia. In the present study, we intended to explore the cholinesterase inhibitory activity of some novel synthesized chalcones, together with their effect on β-amyloid anti-aggregation. Material/Methods: A novel class of chalcone derivatives have been synthesized and characterized by FT-IR,1H-NMR,13C-NMR, and mass and elemental analysis. These derivatives were later used for the determination of acetylcholinesterase (AChE) inhibitory and β-amyloid anti-aggregation activity. Results: The results of the study showed that among the developed compounds, 8g inhibits AChE more prominently than BuChE, as suggested by a selectivity index (SI) of 2.88. Furthermore, the most potent compound, 8g, showed considerable action in inhibition of β-secretase and Aβ aggregation, but not as prominent as that of curcumin as a standard. Conclusions: In conclusion, our study revealed a novel class of chalcone derivatives as a selective inhibitor of AChE with considerably action against β-secretase and Aβ aggregation. Our results may be useful in developing AD drug therapy and warrant further investigation to generate more advanced analogues.

2-PHENYL-3H-IMIDAZO[4,5-B]PYRIDINE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN TYROSINE KINASE ROR1 ACTIVITY

A compound of formula (I′) or (I′′) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of mammalian kinase enzyme activity, including ROR1 tyrosine kinase activity and may be used in the treatment of disorders associated with such activity.

Synthesis and studies on anticonvulsant and antibacterial activities of 1-Alkyl-4-(4H-1,2,4-triazol-4-yl)piperidine derivatives

Two series of 1-Alkyl-4-(4H-1,2,4-triazol-4-yl)piperidines and 1-Alkyl-4-(2H-1,2,4-triazol-3-one-4-yl) piperidines were synthesized and their anticonvulsant and antibacterial activities were evaluated. Pharmacological tests showed that three of the synthesized compounds (6c, 6k, 7m) displayed 100% protection at a dose of 100 mg/kg. 4-(1-Octylpiperidin-4-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (6c) was the most active compound in this study, with an ED50 of 65.4 mg/kg and a TD50 value of 241.2 mg/kg, resulting in a PI of 3.6. Four of the synthesized compounds showed potent inhibitory activity against gram positive bacteria staphylococcus aureus (RN4220, KCTC 209 and KCTC 503), especially against the strains of multidrug-resistant clinical isolates (MRSA3167/3506 and QRSA3505/3519). Among which compound 1-tetradeyl-4-(4H-1,2,4-triazol-4-yl)piperidine (7f) showed the most potent levels of activity (MIC = 2 ug/mL) against the gram-positive strains.

Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position

In this paper, we report the synthesis and cell-based anti-prion activity of quinacrine analogs derived by replacing the basic alkyl side chain of quinacrine with 4-(4-methylpiperazin-I-yl)phenyl, (1-benzylpiperidin-4-yl) and their structural variants. Several promising analogs were found that have a more favorable anti-prion profile than quinacrine in terms of potency and activity across different prion-infected murine cell models. They also exhibited greater binding affinities for a human prion protein fragment (hPrP121-231) than quinacrine, and had permeabilities on the PAMPA-BBB assay that fall within the range of CNS permeant candidates. When evaluated on bidirectional assays on a Pgp overexpressing cell line, one analog was less susceptible to Pgp efflux activity compared to quinacrine. Taken together, the results point to an important role for the substituted 9-amino side chain attached to the acridine, tetrahydroacridine and quinoline scaffolds. The nature of this side chain influenced cell-based potency, PAMPA permeability and binding affinity to hPrP121-231.

Development of a multikilogram synthesis of a chiral epoxide precursor to a CCR1 antagonist. Use of in situ monitoring for informed optimisation via fragile intermediates

The optimisation and scale up of a manufacturing route to a key intermediate, acetic acid 4-acetylamino-3-(2-methyl-oxiranyl- methoxy)phenyl ester (2), utilising a SNAr coupling, the hydro- genation of a nitro moiety and the conversion of a chi

NOVEL BENZODIOXANE AND BENZOXAZINE DERIVATIVES USEFUL AS CC CHEMOKINE RECEPTOR LIGANDS

The present invention relates to benzodioxane and benzoxazine derivatives that act as ligands for CC chemokine receptors, such as CCR1. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

USE OF INTERMEDIATES ((R ) -2,2, 4-TRIMETHYL-L, 3-DIOXOLANE-4-YL) METHANOL (A), 3-F LUORO-4-NITRO-PHENOL (B) AND 1- (4-CHLORO- BENZYL) -PIPERIDIN-4-YLAMINE (C)

The present invention relates to novel processes for the preparation of intermediate compounds which can be used to prepare therapeutic agents. The present invention also relates to novel intermediate compounds which can be used to prepare therapeutic agents. More specifically, the invention relates to the use of intermediates ((R) -2,2,4-trimethyl-l, 3- dioxolane-4 -yl) methanol (A), 3-f luoro-4-nitro-phenol (B) and 1- (4-chloro-benZyl) -piperidin-4-ylamine (C).