2961-50-4

Usage

Uses

Used in Pharmaceutical Industry:
4-N-Amylpyrindine is used as a reactant in the synthesis of bis(pentylpyridinium) compounds, which are known for their antifungal properties. These compounds are particularly effective against a wide range of fungal infections, including Candida, Aspergillus, and dermatophytes. The antifungal activity of bis(pentylpyridinium) compounds is attributed to their ability to disrupt the fungal cell membrane and inhibit the synthesis of ergosterol, an essential component of fungal cell membranes.
In addition to their antifungal properties, bis(pentylpyridinium) compounds have also shown potential as antimicrobial agents against both Gram-positive and Gram-negative bacteria. This dual activity makes them valuable candidates for the development of new antimicrobial drugs to combat the growing problem of antibiotic resistance.
Furthermore, 4-N-Amylpyrindine can be used as a precursor in the synthesis of other bioactive compounds with potential applications in various industries, such as agrochemicals, where it can be used to develop new pesticides or herbicides, or in the development of new materials with specific properties, such as conductive polymers or sensors.

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 1237, 1972 DOI: 10.1016/S0040-4039(01)84556-1

Purification Methods

It is dried with NaOH for several days, then distilled from CaO under reduced pressure, taking the middle fraction and redistilling it. The picrate has m 104o (from EtOH). [Beilstein 20 III/IV 2836.]

Upstream product

• 100-43-6 4-vinylpyridine 
• 29443-43-4 propionaldehyde hydrazone 
• 110-86-1 pyridine 
• 59137-44-9 3-carboxy-2-(pyridin-1-ium-1-yl)propanoate 
• 108-89-4 picoline 
• 542-69-8 1-iodo-butane 
• 693-25-4 n-pentylmagnesium bromide 
• 36938-63-3 5-butyl-5-pyridin-4-yl-pyrimidine-2,4,6-trione 
• 109-69-3 n-Butyl chloride 
• 109-65-9 1-bromo-butane 

Downstream Products

• 84484-26-4 trans-4-(4-n-Pentyl-1-piperidyl)cyclohexan-1-carbonsaeure 
• 84484-24-2 4-(4-n-Pentyl-1-piperidyl)-3-cyclohexen-1-carbosaeure-methylester 
• 84484-27-5 trans-4-(4-n-Pentyl-1-piperidyl)cyclohexan-1-carbonsaeureamid 
• 84484-25-3 trans-4-(4-n-Pentyl-1-piperidyl)cyclohexan-1-carbonsaeure-methylester 
• 102752-50-1 1-benzhydryl-4-pentyl-piperidine; hydrobromide 

Relevant academic research and scientific papers

Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals

The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings

Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.

Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides

An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Δ1-piperideines proceeds in a highly diastereoselective fashion. The Δ1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.

NCN-Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics

Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4-(2,2-dimethylpropyloxy)pyridine (P1), 4-decyloxypyridine (P2), 4-pentylpyridine (P3), 1-decyl-1,2,3-triazole (P4), and 1-benzyl-1,2,3-triazole (P5), are obtained through a Suzuki–Miyaura cross-coupling reaction or CuI-catalyzed 1,3-dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1–P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid-state photo- and electroluminescence characteristics of selected compounds as organic light-emitting diodes are tested. In the guest–host configuration, two matrixes, that is, poly(N-vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD-DFT) provide a deeper understanding of the experimental results.

Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

Sunfish amphiphiles: Conceptually new carriers for DNA delivery

A conceptually new class of cationic amphiphiles, Sunfish amphiphiles, designed for the delivery of genes into cells is introduced. Sunfish amphiphiles have two hydrophobic tails, connected at the 4- and the N-position to the cationic pyridinium headgroup. Two extreme morphologies visualised by backfolding and combining of both tails at one site (matching situation) or unfolding of the tails at distinct interaction sites at biological membranes will lead to considerable differences in morphological behaviour. The underlying rationale allows controlled release by using this morphological alteration of the Sunfish/helper-lipid/DNA complex (lipoplex). The often-excellent transfection efficiencies are probably related to these morphological changes. In addition, the Sunfish amphiphiles possess low toxicities, resulting in high cell survival after internalisation. The underlying rationale, design, synthesis and in vitro transfection potential are discussed in detail. Moreover, some physico-chemical characteristics of the Sunfish amphiphiles have been studied. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Process for preparing fibrinogen receptor antagonists

The invention is a highly efficient synthesis for making compounds of the formula: STR1 wherein: R1 is a six member saturated or unsaturated heterocyclic ring containing one or two heterocyclic atoms wherein the heteroatoms are N; or NR6, wherein R6 is H or C1-10 alkyl; m is an integer from two to six; and R4 is aryl, C1-10 alkyl, or C4-10 aralkyl.

A Convenient Method for the Regioselective Synthesis of 4-Alkyl(aryl)pyridines Using Pyridinium Salts

RCu.BF3 reacted with 1-ethocycarbonylpyridinium chloride at the 4-position with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridine derivatives in high yields (81-94percent).The dihydropyridines were oxidized by oxygen to give 4-alkyl(aryl)pyridines (38-68percent).Grignard reagents also reacted with 1-t-butyldimethylsilylpyridinium triflate with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridines, which were easily oxidized to give 4-substituted pyridines in higher yields than above (58-70percent).