36939-29-4

Upstream product

• 82902-45-2 1-benzoyl-2-phenylpiperidine 
• 100-58-3 phenylmagnesium bromide 
• 76464-88-5 2-(piperidin-1-ylmethyl)phenyl iodide 
• 17642-89-6 1-benzylpiperidine-2-thione 
• 4783-65-7 N-benzyl-2-piperidinone 
• 100-39-0 benzyl bromide 
• 675-20-7 piperidin-2-one 
• 1011-61-6 1-phenylpentane-1,5-diol 
• 100-46-9 benzylamine 
• 98-88-4 benzoyl chloride 
• 3466-80-6 2-phenylpiperidine 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 27845-50-7 (E)-N-benzylidenebenzylamine 

Downstream Products

• 95728-91-9 1-benzyl-2-phenylpiperidine N-oxide 
• 3466-80-6 2-phenylpiperidine 
• 95728-85-1 2-benzyl-7-phenylhexahydro-1,2-oxazepine 

Relevant academic research and scientific papers

Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis

A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

SYNTHETIC PROCESS

The present invention relates to a process for preparing substituted piperidine compounds and especially chiral substituted piperidine compounds. The process involves reacting a substituted pyridinium ion with an amine as defined herein, in the presence o

A simple iridicycle catalyst for efficient transfer hydrogenation of n-heterocycles in water

A cyclometalated iridium complex is shown to catalyse the transfer hydrogenation of various nitrogen heterocycles, including but not limited to quinolines, isoquinolines, indoles and pyridinium salts, in an aqueous solution of HCO2H/HCO2Na under mild conditions. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), with catalyst loadings as low as 0.01 mol % being feasible. Mechanistic investigation of the quinoline reduction suggests that the transfer hydrogenation proceeds via both 1,2- and 1,4-addition pathways, with the catalytic turnover being limited by the step of hydride transfer. An easily accessible iridicycle catalyst effects the transfer hydrogenation of a wide variety of N-heterocycles in water, including quinolines, isoquinolines, indoles, quinoxalines, and pyridines. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), even with low catalyst loadings.

Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation

Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright

Regio- and stereoselective cross-coupling of substituted olefins and imines. A convergent stereoselective synthesis of saturated 1,5-aminoalcohols and substituted piperidines

A mild and efficient alkoxide-directed C-C bond-forming reaction is described that provides a regio- and stereoselective route to 1,5-aminoalcohols based on cross-coupling of substituted olefins and imines. Single and double diastereoselection is explored

An efficient synthesis of nitrogen heterocycles by Cp*Ir-catalyzed N-cycloalkylation of primary amines with diols

A new efficient method for the N-cycloalkylation of primary amines with diols catalyzed by a Cp*Ir complex have been developed. A variety of five-, six-, and seven-membered cyclic amines are synthesized in good to excellent yields in environmentally benign and atom economical manner with the formation of only water as a coproduct. A large scale synthesis of N-benzylpiperidine and a two-step asymmetric synthesis of (S)-2-phenylpiperidine using (R)-1-phenylethylamine as a starting primary amine have been also achieved.

Cp*Ir complex-catalyzed N-heterocyclization of primary amines with diols: A new catalytic system for environmentally benign synthesis of cyclic amines

(Chemical Equation Presented) A new efficient method for the N-heterocyclization of primary amines with diols catalyzed by a Cp*Ir complex was developed. A variety of five-, six-, and seven-membered cyclic amines were synthesized in good to excellent yields with the formation of only water as a byproduct. A two-step asymmetric synthesis of (S)-2-phenylpiperidine was also achieved using (R)-1-phenylethylamine as a starting primary amine.