23019-61-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-4-carboxy-pyridiniuM Ethyl Ester BroMide is used as an intermediate in the synthesis of Iso Guvacine (I819560), which is a GABAA receptor agonist. Its role in the production of this agonist is crucial for the development of potential treatments for various conditions related to the GABAA receptor, such as anxiety, insomnia, and epilepsy.
As an intermediate, 1-Benzyl-4-carboxy-pyridiniuM Ethyl Ester BroMide plays a significant role in the chemical synthesis process, contributing to the development of new pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 1570-45-2 isonicotinic acid ethylester 
• 100-39-0 benzyl bromide 

Downstream Products

• 184900-16-1 1,4-dibenzyl-piperidine-4-carboxylic acid ethyl ester 
• 24228-40-8 N-benzyl isonipecotic acid ethyl ester 
• 23019-62-7 ethyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate 
• 76036-35-6 N-benzyl-4-carbethoxypyridinyl 

Relevant academic research and scientific papers

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation

Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright

Reactions of N-benzyl-pyridinium or -isoquinolinium ylides with ethyl 3-fluoro-3-(fluoroalkyl)acrylates to give fluoroalkyl-substituted indolizine and pyrrolo[2,1-a]isoquinoline derivatives

In the presence of base, N-benzylpyridinium and N-benzylisoquinolinium ylides generated in situ from the N-benzyl-pyridinium or -isoquinolinium bromides react with ethyl 3-fluoro-3-fluoroalkyl(except bromodifluoromethyl)acrylates to give one or two fluoro

Reductive alkylation of pyridinium salts. Part 1. Synthesis of di-, tetra- and hexa-hydropyridine esters

Reaction of 1-methyl-, 1-benzyl- and 1-benzoyl-4-ethoxycarbonylpyridinium salts 1 with zinc and benzyl bromide produce regioselectively the 4,4-disubstituted 1,4-dihydropyridines 3 (R = CH3, PhCH2, PhCO); only the latter is stable but all are reduced catalytically to piperidines 2 (R = CH3, PhCH2, PhCO). 1-Benzoyl-4-ethoxycarbonylpyridinium chloride with zinc and benzoyl chloride or ethyl bromoacetate gives respectively 4-benzoyl- 18 or 4-ethoxycarbonylmethyl-1-benzoyl-4-ethoxycarbonyl-1,4-dihydropyridine 17, but 1-methyl-4-ethoxycarbonylpyridinium iodide 1 (R = CH3, X = I) with benzoyl chloride gives 3-benzoyl-4-ethoxycarbonyl-1-methyl-1,2-dihydropyridine 21.The action of zinc and benzyl bromide on 1-methyl- and 1-benzyl-3-ethoxycarbonylpyridinium salts 5 gives, after catalytic hydrogenation, mixtures of 2- and 4-benzyl-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridines 6 and 7 (R = CH3 or PhCH2) but similar treatment of 1-benzoyl-3-ethoxycarbonylpyridinium chloride 5 (R = PhCO, X = Cl) yields selectively the stable 4-benzyl-3-ethoxycarbonyl-1,4-dihydropyridine 9.Treatment of 1-methyl- or 1-benzoyl-3-ethoxycarbonylpyridinium salts 5 with zinc and benzoyl chloride gives a mixture of products. 1-Methyl-2-ethoxycarbonylpyridinium iodide 11 (R = CH3, X = I) reacts with zinc and benzyl bromide giving, after catalytic hydrogenation, 2-, 4- and 6-benzyl-2-ethoxycarbonyl-1-methylpiperidines 12, 13 and 14 (R = CH3) in the ratio 2:7:1, but 1-benzyl-2-ethoxycarbonylpyridinium bromide 11 (R = PhCH2, X = Br) gives only 1,4-dibenzyl-2-ethoxycarbonylpiperidine 13 (R = PhCH2).

Photochemistry of Stable Pyridinyl Radicals. Photolysis of N-Alkyl-4-(carboalkoxy)pyridinyls

Photoinduced decomposition of N-benzyl-4-carbethoxypyridinyl (1a), N-methyl- (1b) and N-benzyl-4-(carbomethoxy)pyridinyl (1c), and their mixture was studied in degassed acetonitrile.N-benzyl homologues (1a and 1c) were smoothly photolyzed to ethyl (or methyl) isonicotinate by loss of a benzyl group, whereas the N-methyl homologue (1b) was comparatively stable toward UV light; the rate of disappearance of 1c relative to that of 1b was 11:1.A mechanism is postulated, which involves the formation of an alkyl radical by C-N bond homolysis followed by attack on the pyridinyl radical to form dihydropyridines.This is supported by a plot of the yield of ethyl isonicotinate vs. the ratio of initial concentrations 0/0.Pyridinyl radicals 1 possess their absorption maxima at around 300, 395, and 630 nm; those at 300 and 395 nm maxima participate in this reaction.