94977-26-1

Basic information

• Product Name: N-benzyl-1,4-dihydropyridine
• Synonyms: N-benzyl-1,4-dihydropyridine
• CAS NO: 94977-26-1
• Molecular Weight: 171.242
• Mol File: 94977-26-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-benzyl-1,4-dihydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-1,4-dihydropyridine(94977-26-1)
• EPA Substance Registry System: N-benzyl-1,4-dihydropyridine(94977-26-1)

Safety Data

• Hazardous Substances Data: 94977-26-1(Hazardous Substances Data)

Upstream product

• 15519-25-2 1-benzyl-pyridinium 
• 677-22-5 tert-butylmagnesium chloride 
• 2876-13-3 N-benzylpyridinium chloride 

Downstream Products

• 15519-25-2 1-benzyl-pyridinium 
• 4217-54-3 9,10-dihydro-10-methylacridine 

Relevant articles and documents

Formation of η2-coordinated dihydropyridine-ruthenium(II) complexes by hydride transfer from ruthenium(II) to pyridinium cations

Reactions between various pyridinium cations with and without a -CF 3 substituent at the 3-position and [Ru(tpy)(bpy)H]+ (tpy = 2,2′:6′,2″-terpyridine and bpy = 2,2′-bipyridine) were investigated in detail. The corresponding 1,4-dihydropyridines coordinating to a Ru(II) complex in η2 mode through a C=C bond were quantitatively formed at the initial stage. The only exception observed was in the case of the 1-benzylpyridinium cation, where a mixture of two adducts with 1,4-dihydropyridine and 1,2-dihydropyridine was formed in the ratio 96:4. Cleavage of the Ru-(C=C) bond proceeded at a slower rate in all reactions, giving the corresponding dihydropyridine and [Ru(tpy)(bpy)(NCCH 3)]2+ when acetonitrile was used as a solvent. Kinetic activation parameters for the adduct formation indicated that the 1,4-regioselectivities were induced by formation of sterically constrained structures.

Mechanism of the Grignard Addition Reaction. XV. The Reaction of Grignard Reagents with Benzylpyridinium Chloride

The reaction of Grignard reagents with benzylpyridinium chloride produces 2-alkyl-N-benzyl-1,2- and 4-alkyl-N-benzyl-1,4-dihydropyridines.The mechanism seems to be polar, concerted except for the t-butylmagnesium reagent.The adducts may reduce the starting material to the unreported, non-alkylated N-benzyl-1,4-dihydropyridine.If the Grignard-alkyl is secondary, crystalline 4-alkylidene-1,4-dihydropyridines may be produced.Thermal rearrangements of N-benzyl-1,4-dihydropyridines lead to migration of the benzyl group.