21057-43-2

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 106-95-6 allyl bromide 

Downstream Products

• 92-54-6 4-phenyl-1-piperazine 
• 1442941-92-5 1-{3-[dimethyl(5-diethoxymethylfuran-2-yl)silyl]propyl}-4-phenylpiperazine 
• 1442942-27-9 1-{3-[dimethyl(5-phenylfuran-2-yl)silyl]propyl}-4-phenylpiperazine 
• 1223769-93-4 2-{[3-(4-phenylpiperazino)propyl]dimethylsilyl}-5-triethylsilylfuran 

Relevant academic research and scientific papers

Click chemistry on solid support: Synthesis of a new REM resin and application for the preparation of tertiary amines

1,3-Dipolar cycloaddition was employed for the synthesis of a highly practical REM resin. Exploiting this concept, the resulting triazolylmethyl acrylate (TMA) resin was used for an efficient parallel synthesis of tertiary amines by Michael addition, subs

Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/fischer indole synthesis

The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

Ruthenium-Catalyzed Chemoselective N-Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic Amines

A novel application of the Grubbs carbene complex has been discovered. The first examples of the catalytic deprotection of allylic amines with reagents other than palladium catalysts have been achieved through Grubbs carbene mediated reaction. Significantly, the catalytic system directs the reaction toward the selective deprotection of allylic amines (secondary as well as tertiary) in the presence of allylic ethers. A variety of substrates, including enantiomerically pure multifunctional piperidines, are also usable. The new method is more convenient, chemoselective, and operationally simple than the palladium-catalyzed method. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that the reactive species involved in the reaction may be an Ru-H species rather than the Grubbs carbene itself. Thus, the isomerization may occur according to the hydride mechanism. The synthetic utility of this ruthenium-catalyzed allyl cleavage is illustrated by the preparation of indolizidine-type alkaloids.

Solution-phase combinatorial synthesis of isoxazolines and isoxazoles using [2+3] cycloaddition reaction of nitrile oxides

An efficient way to construct a library of isoxazoles and isoxazolines was developed by solution-phase 1,3-dipolar cycloaddition reaction of nitrile oxides with olefins and alkynes followed by precipitation of the products as HCl salts.

Soluble polymer bound cleavage reagents: A multipolymer strategy for the cleavage of tertiary amines from REM resin

(equation presented) Soluble polymer bound reagent 1 has been prepared to cleave tertiary amines from REM resin. Normally, amines cleaved from REM resin require extraction or chromatography to remove excess cleavage reagent and its byproducts. The solubility profile of non-crosslinked polystyrene (NCPS) based reagent 1 eliminates the need for such purification and allows for the direct isolation of a library of pure tertiary amines through simple filtration and concentration operations.

Asymmetric ethylmagnesiation of alkenes using a novel zirconium catalyst

The novel C1-symmetric zirconocene CpCp°ZrCl2 (Cp=C5h5, Cp°= 1- neomenthyl-4, 5, 6, 7-tetrahydroindenyl) is a cheap, active, and effective catalyst for the asymmetric ethylmagnesiation of unactivated terminal alkenes.

Synthesis of tertiary amines using a polystyrene (REM) resin

A range of tertiary amines was constructed using a 'traceless' linker on a polystyrene resin (REM resin), starting from seconday amines, primary amines, and resin-bound 'ammonia'. The methodology is characterized by three essential steps conducted under ambient conditions: (1) coupling of the starting amine (Michael addition) to the resin, (2) activation (quaternization), and (3) cleavage of the product amine (Hofmann elimination). The linker is compatible with both acid and base sensitive protecting group strategies. The nature of the chemistry ensures that the tertiary amine products are obtained in consistently high purity (95% or greater). After cleavage of the product, REM resin is regenerated and can be reused for repeat syntheses. The yield and purity of repeat batches is maintained over 5 cycles, allowing the automated synthesis of >0.5 g quantities of pure tertiary amine.

A novel linker strategy for solid-phase synthesis

The REM resin for solid phase synthesis is described. Its use is illustrated by preparing a small array of tertiary amines using a Hoffman elimination reaction. No functional group is required for linking these compounds onto the resin other than the amin