3333-08-2

Usage

Chemical Class

Quaternary ammonium salts

Common Use

Phase-transfer catalyst in organic synthesis

Specific Application

Alkylation reactions of nucleophiles with alkyl halides

Key Ability

Facilitating transfer of reactants between immiscible phases

Result

Efficient and selective chemical transformations

Additional Utilization

Synthesis of pharmaceuticals and other organic compounds

Catalytic Properties

Enhances chemical reactions and transformations

InChI:InChI=1/C7H16N.HI/c1-8(2)6-4-3-5-7-8;/h3-7H2,1-2H3;1H/q+1;/p-1

Upstream product

• 110-89-4 piperidine 
• 74-88-4 methyl iodide 
• 626-67-5 N-methylcyclohexylamine 
• 880-09-1 di(N-piperidinyl)methane 
• 4703-22-4 N-tosylpiperidine 
• 67-64-1 acetone 
• 186581-53-3 diazomethane 
• 81926-17-2 1-(5-Acetylamino-2-hydroxy-benzyl)-1-methyl-piperidinium; iodide 
• 6214-23-9 methyl (2Z)-3-iodoprop-2-enoate 
• 13886-01-6 N-(4-Hydroxy-3-piperidinomethylphenyl)acetamid 
• 618-38-2 benzoyl iodide 

Downstream Products

• 626-67-5 N-methylcyclohexylamine 
• 24307-26-4 mepiquat chloride 
• 618-42-8 1-piperidin-1-yl-ethanone 

Relevant academic research and scientific papers

13C Chemical Shifts and Conformational Equilibria in Quaternary Piperidinium Salts

Carbon-13 nuclear resonance spectra of a series of N-methyl-N-alkylpiperidinium salts have been measured, and the observed chemical shifts analysed in terms of the stereochemical and conformational properties of the molecules.Furthermore, the differences of the free energy (ΔGo) between two conformers on ring inversion have been estimated.

Insight into the Alkaline Stability of N-Heterocyclic Ammonium Groups for Anion-Exchange Polyelectrolytes

The alkaline stability of N-heterocyclic ammonium (NHA) groups is a critical topic in anion-exchange membranes (AEMs) and AEM fuel cells (AEMFCs). Here, we report a systematic study on the alkaline stability of 24 representative NHA groups at different hydration numbers (λ) at 80 °C. The results elucidate that γ-substituted NHAs containing electron-donating groups display superior alkaline stability, while electron-withdrawing substituents are detrimental to durable NHAs. Density-functional-theory calculations and experimental results suggest that nucleophilic substitution is the dominant degradation pathway in NHAs, while Hofmann elimination is the primary degradation pathway for NHA-based AEMs. Different degradation pathways determine the alkaline stability of NHAs or NHA-based AEMs. AEMFC durability (from 1 A cm?2 to 3 A cm?2) suggests that NHA-based AEMs are mainly subjected to Hofmann elimination under 1 A cm?2 current density for 1000 h, providing insights into the relationship between current density, λ value, and durability of NHA-based AEMs.

Cucurbit[7]uril host-guest complexes and [2]pseudorotaxanes with N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution

The formations of host-guest complexes between cucurbit[7]uril and a series of N-substituted N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution have been investigated using 1H NMR spectroscopy and electrospray ionization mass spectrometry. Dications comprising the N-methylheterocyclic head groups, bridged by a decamethylene chain, form sequential 1:1 ([2]pseudorotaxanes) and 2:1 host-guest complexes with cucurbit[7]uril. The cucurbituril initially resides over the decamethylene chain, however with further additions of the host molecule a translocation of the hosts to the cationic N-heterocyclic head groups occurs. The order of the magnitude of the cucurbituril host-guest stability constants, determined by competitive 1H NMR binding experiments, follows the trend in the hydrophobicity of the quaternary ammonium cations.

Acyl iodides in organic synthesis. Reactions with morpholine, piperidine, and N-hydrocarbylpiperidines

Acyl iodides RCOI (R = Me, Ph) reacted with morpholine and piperidine to give the corresponding N-acyl derivatives and morpholine or piperidine hydroiodides. Reactions of acyl iodides with N-methyl- and N-ethylpiperidines involved cleavage of the exocyclic R-N bond with formation of N-acylpiperidine and alkyl iodide and were accompanied (to insignificant extent) by cleavage of the endocyclic N-C bond, leading to N-alkyl-N-(5-iodopentyl)acylamides. In the reaction of acetyl iodide with N-phenylpiperidine, the main process was cleavage of just endocyclic N-C bond to produce N-(5-iodopentyl)-N-phenylacetamide and its dehydroiodination product, N-(pent-4-en-1-yl)-N-phenylacetamide. Analogous reaction with benzoyl iodide afforded N-(5-iodopentyl)-N-phenylbenzamide in a poor yield.

Dealkylation of Quaternary Ammonium Salts by Thiolate Anions: A Model of the Cobalamin-independent Methionine Synthase Reaction.

The reactions of thiolate ions derived from thiophenol and homocysteine with substituted quaternary ammonium salts result in alkyl transfer from nitrogen to sulfur.A radical mechanism for this transalkylation, accounts for the reactivity pattern of the substrate salts.In a model study of the cobalamin-independent methionine synthase reaction, 5,5,6,7-tetramethyl-5,6,7,8-tetrahydropteridinium salt (25), which can be considered as a model for the natural coenzyme 5-CH3H4-folate (1), was allowed to react with the thiolate of homocysteine, whereupon the formation of methionine was observed in good yield.These results suggest that in the enzymatic process the N(5)-CH3 bond may be activated for the methyl transfer step, by coordination of the N(5) with an electrophile or a proton at the active site.

Synthesis of Dihydrobenzofurans from Phenolic Mannich Bases and their Quaternized Derivatives

Reaction of dimethylsulphoxonium methylide with quaternized derivatives of phenolic Mannich bases, and in certain cases with the bases themselves, constitutes a useful synthesis of dihydrobenzofurans.On the other hand treatment of those same quaternized derivatives with diazomethane may be a useful alternative procedure for the preparation of coumarans with base-sensitive groups.

Kinetics of Reactions of Cyclic Secondary Amines with 2,4-Dinitro-1-naphthyl Ethyl Ether in Dimethyl Sulfoxide Solution. Spectacular Difference between the Behavior of Pyrrolidine and Piperidine

The reactions named in the title, which form N-(2,4-dinitro-1-naphthyl) derivatives of these heterocyclic amines, occur in two distinct stages.In stage I, the spectrum of a ?-adduct intermediate develops at a rate which is measurable in a stopped flow apparatus; in stage II, it decays at a slower and easily measurable rate.The kinetics of both stage I and stage II have been studied.Pyrrolidine and piperidine are similar in their stage I behavior, but reactivity in stage II is about 11000 times greater in the pyrrolidine system.This huge difference between systems apparently so similar is judged to arise from steric interactions forced by differences in conformation between the amino moieties in the intermediate ? adducts as they release the nucleofuge.It calls into question the rate-limiting proton transfer interpretation of base catalysis in analogous aminodephenoxylation reactions in protic solvents.