175441-83-5

Basic information

• Product Name: N-(DIPHENYLMETHYLENE)-N-[(5-METHYLPYRIDIN-3-YL)METHYL]AMINE
• Synonyms: N-(DIPHENYLMETHYLENE)-N-[(5-METHYLPYRIDIN-3-YL)METHYL]AMINE;N-(DiphenylMethylene)-3-pyridineMethanaMine
• CAS NO: 175441-83-5
• Molecular Formula: C₁₉H₁₆N₂
• Molecular Weight: 286.37
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 175441-83-5.mol

Chemical Properties

• Melting Point: 262-268 °C(Solv: ethanol (64-17-5))
• Boiling Point: 410.7±37.0 °C(Predicted)
• Appearance: /
• Density: 1.03±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.93±0.10(Predicted)
• CAS DataBase Reference: N-(DIPHENYLMETHYLENE)-N-[(5-METHYLPYRIDIN-3-YL)METHYL]AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(DIPHENYLMETHYLENE)-N-[(5-METHYLPYRIDIN-3-YL)METHYL]AMINE(175441-83-5)
• EPA Substance Registry System: N-(DIPHENYLMETHYLENE)-N-[(5-METHYLPYRIDIN-3-YL)METHYL]AMINE(175441-83-5)

Safety Data

• Hazardous Substances Data: 175441-83-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(Diphenylmethylene)-N-[(5-Methylpyridin-3-yl)Methyl]Amine is used as a synthetic building block for the development of a wide range of organic compounds. Its unique chemical structure allows it to participate in various chemical reactions, facilitating the formation of complex molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(Diphenylmethylene)-N-[(5-Methylpyridin-3-yl)Methyl]Amine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form a diverse array of organic molecules makes it a valuable asset in the development of new drugs with potential therapeutic benefits.
Used in Chemical Research:
N-(Diphenylmethylene)-N-[(5-Methylpyridin-3-yl)Methyl]Amine is also employed in chemical research as a tool to study the properties and reactivity of different organic molecules. Its use in research helps scientists gain a deeper understanding of chemical reactions and mechanisms, ultimately contributing to the advancement of the field.
Used in Material Science:
In the field of material science, N-(Diphenylmethylene)-N-[(5-Methylpyridin-3-yl)Methyl]Amine is used as a component in the development of novel materials with specific properties. Its incorporation into these materials can lead to improved performance characteristics, such as enhanced stability, reactivity, or selectivity.

Upstream product

• 3731-52-0 3-Aminomethylpyridine 
• 119-61-9 benzophenone 
• 500-22-1 3-pyridinecarboxaldehyde 
• 946164-43-8 allyl 2,2-diphenylglycinate 
• 946164-41-6 C₂₅H₂₃NO₄ 
• 1013-88-3 Benzophenone imine 
• 3060-50-2 2,2-diphenylglycine 

Downstream Products

• 1027559-83-6 Benzhydrylidene-((Z)-5-chloro-1-pyridin-3-yl-pent-3-enyl)-amine 
• 1027550-42-0 α<3-(ethoxy)propyl>-3-pyridinemethaneamine 
• 5746-86-1 rac-nornicotine 
• 2743-90-0 (+/-)-Anatabine 
• 13078-04-1 anabasine 

Relevant articles and documents

Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.

Preparation method for anatabine

The invention discloses a preparation method for anatabine. The method comprises the steps of (1) enabling 3-amino methyl pyridine to react with benzophenone to obtain an intermediate 1; (2) synthesizing an intermediate 2 by the intermediate 1 and cis-1,4-dichloro-2-butene; (3) enabling the intermediate 2 to react with Boc anhydride to obtain an intermediate 3; and (4) removing a Boc group from the intermediate 3 to obtain an intermediate 4 to obtain an anatabine product. The anatabine prepared by adopting the method is high in yield, high in purity and good in quality.

ALKALOID COMPOUNDS FOR TREATING DEPRESSION, SUBSTANCE ADDICTIONS, AND INDICATIONS ASSOCIATED WITH CHRONIC INFLAMMATION

Alkaloid compounds described herein are useful for treating disorders associated with monoamine oxidase (MAO) activity, such as depression, pain, smoking cessation, and substance addictions, and/or for treating disorders associated with chronic or low-level inflammation. In some examples, compounds are effective for treating cancers, autoimmune disorders, and other disorders associated with inducible nitric oxide synthase (iNOS).

METHODS OF SYNTHESIZING ANATABINE

Anatabine is obtained by reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine. The resulting anatabine is substantially free from contaminants and displays good stability. In an alternative embodiment, the benzylhydrylidene-pyridin-3-yl-methyl-amine may be used in the synthesis of other alkaloids such as anabasine, nornicotine, N-methylanabasine, and anabaseine.

Synthesis and characterization of some heterocyclic schiff bases: Potential anticonvulsant agents

A series of novel schiff bases of 3-aminomethyl pyridine have been synthesized through condensation reaction with substituted aryl aldehydes/ketones and/cyclic ketones. These schiff bases were screened for anticonvulsant activity. The chemical structures of synthesized compounds were confirmed by FT-IR, 1H-NMR, spectroscopy, and elemental analysis. A number of compounds were observed to exhibit seizures protection after intraperitoneal administration at the dose 30 and 100 mg kg-1 in various models employed. In MES screen we found five potent compounds i.e., (1c) N-(2-chlorobenzylidene) (pyridin-3-yl) methanamine, (1 f) 2-methoxy-4-{(pyridine-3-ylmethyl imino) methyl} phenol, (2 a) N-(3phenylallylidene) (pyridin-3-yl) methanamine, (3b) 3-{1-(pyridin-3-ylmethylimino) ethyl} benzenamine, and (4a) N-(diphenyl-methylene) (pyridin-3- yl) methanamine, emerged as most active compounds in series (ED50) 11.70, 6.39, 11.70, 8.64, and 9.13 mg kg-1 with high protective index (PI)>10. Four compounds (1 e) 4-{(Pyridine-3-ylmethylmino) methyl}benzene-1,3-diol, (1 g) N-(3,4,-dimethoxybenzylidene) (pyridin-3-yl)methanamine, (2 b) N-{(1H-indol-3-yl)methylene}(pyridin-3-yl) methanamine, and (5) N-cyclohexylidene (pyridine-3-yl) methanamine) showed remarkable protection over clinically used drugs in sc.PTZ screen (ED50) 6.44, 11.70, 6.47, and 14.16 with (PI>10). Compound (4b) showed good anticonvulsant activity (ED50) 20.79, but with relatively higher neurotoxicity (PI, 0.57). Compound (le) was active in both sc.PTZ and in sc.STR seizures. Some selected compounds were subjected to oral MES screen (30 mg kg-1) in rats, most of the compounds showed peak activity after 0.5 h of oral administration. Springer Science+Business Media, LLC 2010.

Evaluation of structurally diverse neuronal nicotinic receptor ligands for selectivity at the α6* subtype

Direct comparison of pyridine versus pyrimidine substituents on a small but diverse set of ligands indicates that the pyrimidine substitution has the potential to enhance affinity and/or functional activity at α6 subunit-containing neuronal nicotinic rece

C-C bond-forming reactions via Pd-mediated decarboxylative α-lmino anion generation

α-lmino anions are generated under neutral reaction conditions via a Pd-mediated decarboxylation of allyl diphenylglycinate imines with concomitant formation of a π-allylpalladium species. The resulting delocalized anion can attack the π-allyl-Pd(ll) spec

A practical one-pot synthesis of trans-4,5-disubstituted 2-pyrrolidinones and the related pyrrolidines

A practical and general method for the stereoselective synthesis of trans-4,5-disubstituted 2-pyrrolidinones was developed. Hydride reduction of these pyrrolidinones gave the corresponding pyrrolidines.

Regioselective alkylation of N-(diphenylmethylidine)-3-(aminomethyl)pyridine: A simple route to minor tobacco alkaloids and related compounds

A simple synthetic route to minor tobacco alkaloids and related compounds is described involving regioselective alkylation of N-(diphenylmethylidine)-3-(aminomethyl)pyridme with a suitable dielectrophile.