1026504-57-3

Upstream product

• 771-99-3 4-phenylpiperidine 
• 874493-33-1 pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate 
• 142-08-5 2-hydroxypyridin 
• 372-48-5 2-fluoropyridine 
• 10272-49-8 4-phenylpiperidine hydrochloride 

Downstream Products

• 1401997-72-5 2-(2,6-dihexyl-4-phenylpiperidin-1-yl)pyridine 
• 1631043-20-3 cis/Cis-2-{2,6-bis[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-4-phenylpiperidin-1-yl}pyridine 
• 1631043-21-4 trans/trans-2-{2,6-bis[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-4-phenylpiperidin-1-yl}pyridine 

Relevant academic research and scientific papers

Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides

The amination of various phosphorodiamidate-substituted pyridines, quinolines, and quinoxaline with magnesium amides R2NMgCl·LiCl proceeds at room temperature within 8 h. Several pharmaceutically active amines were suitable substrates for this amination procedure, and also the antihistaminic tripelennamine was prepared. Additionally, several heterocyclic phosphorodiamidates underwent directed ortho-metalation (DoM) using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) or TMP2Mg·2LiCl, followed by electrophilic functionalization prior to the amination step, which led to ortho-functionalized aminated N-heterocycles.

The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H α-alkylation of cyclic amines

A general directed Ru-catalyzed C(sp3)-H α-alkylation protocol for piperidines (less-reactive substrates than the corresponding five-membered cyclic amines) has been developed. The use of a hindered alcohol (2,4-dimethyl-3-pentanol) as the solvent and catalyst activator, and a catalytic amount of trans-1,2-cyclohexanedicarboxylic acid is necessary to achieve a high conversion to product. This protocol was used to effectively synthesize a number of 2-hexyl- and 2,6-dihexyl piperidines, as well as the alkaloid (±)-solenopsin A. Kinetic studies have revealed that the carboxylic acid additive has a significant effect on catalyst initiation, catalyst longevity, and reverses the reaction selectivity compared with the acid-free reaction (promotes alkylation versus competing alkene reduction). Acid makes the difference! A directed Ru-catalyzed C(sp3)-H α-alkylation protocol for cyclic amines has been developed (see scheme). Kinetic studies revealed that the carboxylic acid aids catalyst activation, increases catalyst longevity, and reverses the reaction selectivity. The alcohol selected as the solvent plays an active role in the catalysis. Copyright