70263-43-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 3479, 1981 DOI: 10.1021/jo00330a019

Upstream product

• 108-86-1 bromobenzene 
• 593-60-2 Vinyl bromide 
• 14548-45-9 (4-bromophenyl)-pyridin-3-yl-methanone 
• 1826-67-1 vinyl magnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 10400-19-8 3-pyridinecarbonyl chloride 

Downstream Products

• 91671-09-9 Bis-[(E)-3-(4-bromo-phenyl)-3-pyridin-3-yl-allyl]-methyl-amine 
• 83049-64-3 (E)-3-(4-Bromophenyl)-3-(3-pyridyl)propenal 
• 56775-89-4 (E)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 79567-81-0 (Z)-3-[4-(trimethylsilyl)phenyl]-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 79567-85-4 (Z)-3-(4-cyanophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 79567-83-2 (Z)-3-[4-(methylthio)phenyl]-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 79362-30-4 I-ZIM 
• 79567-79-6 (Z)-3-(4-methylhenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 56775-88-3 Zimelidine 
• 58574-55-3 (Z)-1-(3-Pyridyl)-1-phenyl-3-dimethylamino-propen 
• 82103-82-0 (Z)-1-(4-bromophenyl)-3-pthalimido-1-(3-pyridyl)propene 
• 82103-83-1 (E)-1-(4-bromophenyl)-3-pthalimido-1-(3-pyridyl)propene 
• 60324-67-6 (Z)-3-(4-bromophenyl)-3-(3-pyridyl)allylamine 
• 77470-68-9 (Z)-3-(4-bromophenyl)-3-(3-pyridyl)-2-propenal 

Relevant academic research and scientific papers

Synthesis of 3-Aryl-3-pyridylallylamines Related to Zimelidine via Palladium-Catalyzed Amination

Reaction of aryl pyridyl ketones 1 with vinylmagnesium bromide followed by acetylation of the products 2 with acetic anhydride/Et3N and with 4-(dimethylamino)pyridine (DMAP) as a catalyst gave acetates 3 in high yields.Treatment of acetates 3 with dimethylamine in the presence of a palladium catalyst produced a mixture of E and Z isomers of 3-aryl-3-pyridylallylamines 4.

Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake

Analogues of the antidepressant agent zimelidine [6, (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine], a selective inhibitor of neuronal 5-hydroxytryptamine reuptake, were synthesized by several routes with the aim of obtaining compounds having a cis configuration (with respect to pyridyl and allylamine). Two methods utilized suitably substituted benzoylpyridines as starting materials. In two other routes, the bromine in 6 was either directly displaced (CN) or converted via the corresponding lithio derivative to H, Cl, I, Me, SiMe3. The configurations were determined by UV, 1H NMR and lanthanide-induced shifts in 1H NMR. The compounds were evaluated as uptake inhibitors by measuring the accumulation of [3H]noradrenaline and 5-hydroxyl[14C]tryptamine in mouse brain slices (in vitro and in vivo). Para substitution favored 5-hydroxytryptamine activity and ortho substitution favored NA activity in the cis series. The in vitro effect on 5-hydroxytryptamine was rather insensitive to variations in the para substituent, whereas pronounced effects in vivo were observed only with Cl, Br (6), and I.

Novel intermediate for preparation of therapeutically active compounds

A novel compound of the formula STR1 useful in the preparation of therapeutically active compounds, especially compounds useful as antidepressive agents; a process for preparation of said compound and a process for preparing therapeutically active compounds employing said compound as an intermediate.