33216-40-9

Upstream product

• 101-82-6 2-Benzylpyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 137024-07-8 2-benzyl-1-methyl-1,4-dihydro-4-(5-oxo-2-phenyl-2-oxazolin-4-yl)pyridine 
• 101-82-6 2-Benzylpyridine 
• 14925-09-8 2-(N-methylamino)-1,1'-biphenyl 
• 90-43-7 2-Phenylphenol 
• 77989-56-1 N-ethyl-[1,1'-biphenyl]-2-amine 
• 4636-73-1 triethylammonium iodide 
• 554-68-7 triethylamine hydrochloride 
• 575-19-9 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine 
• 107534-98-5 2-benzyl-1-methyl-1,2,5,6-tetrahydropyridine 
• 137024-11-4 5-(2-benzyl-1-methyl-1,4-dihydropyridin-4-yl)-2,3-diphenyl-4-thiazolidone 
• 51859-08-6 2-benzylidene-1-methyl-1,2-dihydro-pyridine 

Relevant academic research and scientific papers

Syntheses of the opioid substructures 1,2,3,4,5,6-hexahydro-2,6-methano-3- benzazocine and 2,3,4,5-tetrahydro-1,5-methano-1H-2-benzazepine

Concise syntheses of 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (12) and 2,3,4,5-tetrahydro-1,5-methano-1H-2-benzazepine (18) are described and involve an intramolecular Friedel-Crafts alkylation and an intramolecular Heck cyclization as their respec

Strained heterocyclic systems. Part 21. The Menschutkin reaction

Rate constants are determined for methyl iodide quaternisations of a series of 2-substituted quinolines and pyridines. Relative rates are interpreted in terms of steric effects, electronic effects and calculated geometries.

Reaction of N-alkylpyredinium salts with phosphorus trichloride

1-Alkylpyridinium bromides 1 having activated N-methylene group react with phosphorus trichloride to give N-(dichlorophosphinomethylene)pyridinium ylides 2. The site of the reaction in 1,2-dialkylpyridinium halides 3 under these conditions is determined by the relative activation of 1- and 2-methylene groups; in the absence of sufficient activation of N-methylene group, reaction occurs at the 2-methylene group to give dichlorophosphinylated anhydrobases 5 and 11. 1,4-Dialkylpyridinium bromide 13 behaves analogously to give the corresponding dichlorophosphinylated anhydrobase 14.

Enamine Rearrangement of 2-Benzylpyridinium Salts to 2-Aminobiphenyls

N-Methyl-2-benzylpyridinium iodide (1c) undergoes ring opening and recyclization reactions when heated with methylammonium sulphite to give 2-methylaminobiphenyl (2c), 2-hydroxybiphenyl (3) and 2-benzylpyridine (4).A similar reaction of N-methyl-2-(p-acetylbenzyl)-, N-methyl-2-(p-acetamidobenzyl)-, N-methyl-2-(p-phthalimidobenzyl)-, N-methyl-2-(p-ethylaminobenzyl)-, N-methyl-2-(p-methylethylaminobenzyl)-, and N-methyl-2-butyl-pyridinium iodides (1e, g-k) affords 2-methylamino-4-acetylbiphenyl (2e), 2-methylamino-4-aminobiphenyl (2g = 2h), 2-methylamino-4-ethylaminobiphenyl (2i), 2-methylamino-4-methylethylaminobiphenyl (2j) and N-methyl-2-propylaniline (2k) respectively in good yields.On the other hand, N-methyl-2-(carbamylmethyl)- (1a), N-methyl-2-(cyanomethyl)- (1b) and N-methyl-2-(p-nitrobenzyl)pyridinium iodides (1d) do not undergo such a rearrangement.It has been found that the unquaternized 2-benzylpyridine when heated with methylammonium sulphite undergoes recyclization to 2-methylaminobiphenyl (2k).