3088-41-3

Usage

Chemical Properties

clear golden liquid

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 349, 1982 DOI: 10.1016/S0040-4039(00)86828-8

InChI:InChI=1/C8H14N2/c9-5-4-8-10-6-2-1-3-7-10/h1-4,6-8H2/p+1

Upstream product

• 110-89-4 piperidine 
• 110-67-8 3-Methoxypropionitrile 
• 34583-60-3 p-CH₃C₆H₄-O₂SO-CH₂CH₂CN 
• 107-13-1 acrylonitrile 
• 109-78-4 3-Hydroxypropionitrile 
• 1738-25-6 3-dimethylaminopropiononitrile 
• 2417-90-5 bromopropionitrile 

Downstream Products

• 5452-83-5 2-[2-(piperidyl)ethyl]pyridine 
• 139541-16-5 β-piperidinopropionic acid amidoxime 
• 928988-30-1 N-acetyl-sulfanilic acid-(3-piperidino-propylamide) 
• 94823-13-9 dichloro-acetic acid-[(2,4-dichloro-benzyl)-(3-piperidino-propyl)-amide] 
• 107418-90-6 dichloro-acetic acid-[(4-chloro-benzyl)-(3-piperidino-propyl)-amide] 
• 94801-82-8 (3-piperidino-propyl)-veratryl-amine 
• 97753-68-9 (2,4-dichloro-benzyl)-(3-piperidino-propyl)-amine 
• 111163-12-3 4-chloro-2-[(3-piperidino-propylamino)-methyl]-phenol 
• 23061-67-8 N-phenyl-N'-(3-piperidino-propyl)-thiourea 
• 111585-13-8 (2-chloro-benzyl)-(3-piperidino-propyl)-amine 
• 111584-72-6 (4-chloro-benzyl)-(3-piperidino-propyl)-amine 
• 4801-58-5 N-hydroxypiperidine 
• 71-43-2 benzene 
• 113802-25-8 4-Phenyl-3-piperidin-1-ylmethyl-quinolin-2-ylamine 

Relevant academic research and scientific papers

Fluorescent non-imidazole histamine H3 receptor ligands with nanomolar affinities

ω-Piperidinoalkanamine derivatives with fluorescent moieties (2-cyanoisoindol-1-yl, 7-nitrobenzofurazan-4-yl) have been synthesized starting from piperidine in three steps. The compounds display moderate to good histamine hH3 receptor affinities with Ki values ranging from 178 to 11 nM. The new compounds may act as tools for identification and understanding of the binding site on the histamine H3 receptor.

Haliclorensin, a novel diamino alkaloid from the marine sponge Haliclona tulearensis

Haliclorensin (1), a novel diamino alkaloid possessing an azacyclodecane ring, has been isolated from the sponge Haliclona tulearensis. Its structure was elucidated on the basis of spectroscopic data, as well as by comparison with γ-amino azacycloalkanes.

Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature

A pure cellulose was derived from waste fibre and it was chemically modified to a hydroxamic acid ligand. The poly(hydroxamic acid) was treated with an aqueous copper solution to afford the greenish stable five-membered copper complex; namely Cu(II)@PHA. Further, the Cu(II)@PHA was treated with a reducing agent hydrazine hydride to give brown colour cellulose supported copper nanocomplex (Cu(0)NC@PHA). The Cu(0)NC@PHA was characterised by ATR-FTIR, FE-SEM & EDS, TEM, ICP-OES, TGA, XRD and XPS analyses. The cellulose-based Cu(0)NC@PHA was used for the n-aryl/alkylation (Michael addition) reaction with a variety of α,β-unsaturated Michael acceptors to produce the corresponding n-aryl/alkyl products with an excellent yield at room temperature. The Cu(0)NC@PHA showed extraordinary stability and it was easily filtered out from the reaction mixture and may potentially recycled up to five times without loss of its original catalytic ability.

Green synthesis of Ag@Au bimetallic regenerated cellulose nanofibers for catalytic applications

The green synthesis of nanocomposites has attracted huge consideration in recent years due to its positive environmentally friendly impact. The present study reports the first bimetallic Ag-Au cellulose nanofiber composite (Ag@Au/CNCs) prepared via a very simple green preparation method. An aqueous leaves extract of Moringa oleifera was used to obtain the bimetallic Ag@Au/CNC nanocomposite. High-resolution transmission electron microscopy (HRTEM) observations revealed the successful formation of triangle, hexagonal, and spherical shapes of well-combined Ag-Au nanoparticles on the regenerated cellulose nanofiber surface. Further, the formation of Au-Ag bimetallic nanostructures was confirmed by X-ray photoelectron spectroscopy (XPS) and X-ray crystallography (XRD) results. The resultant bimetallic Ag@Au/CNC catalyst was found to perform remarkably well in the reduction of nitrophenols. The bimetallic Ag@Au/CNC catalyst gave excellent kapp values of 15.59 and 22.83 × 10-3 s-1 for the 2- A nd 4-nitrophenol reduction process, respectively. To our delight, the Ag@Au/CNC catalyst was found to perform well in the aza-Michael reaction. The catalytic activity of Ag@Au/CNCs was compared with mono-metallic Ag/CNCs, Au/CNCs, and other reported catalysts. Based on the results obtained, the high synergy of Ag@Au/CNCs was explained. A possible mechanism is proposed for the Ag@Au/CNC-catalyzed nitrophenol reduction and aza-Michael reactions.

Cultivation of a Cu/HMPC catalyst from a hyperaccumulating mustard plant for highly efficient and selective coupling reactions under mild conditions

Cu-containing activated carbon (eco-catalyst, Cu/HMPC, where 'C' defines 'carbon') was derived from a metal-hyperaccumulating mustard plant (HMP) by a simple chemical activation method. Transmission electron microscopy/selected area diffraction (HRTEM/SAED) results revealed that the Cu/HMPC has mainly three types of morphology [sheet-like morphology (2D), hollow-spheres (3D) and needle-like structures (1D)] which are interconnected. HRTEM-SAED, Raman and X-ray photoelectron spectroscopy (XPS) results confirmed the existence of Cu oxide species in Cu/HMPC. Content of Cu in Cu/HMPC was determined to be 1.03 wt%. The quality of graphitization in Cu/HMPC was discussed by using Raman and XRD results. The BET surface area of Cu/HMPC was determined to be 620.8 m2 g-1. The Cu/HMPC actively transformed a wide range of amines to imines under very mild reaction conditions. The catalyst Cu/HMPC gave products in excellent yields (98-61%) with very high TON/TOF values (1512/339-833/35 h-1). To the best of our knowledge, this is the most efficient Cu-based heterogeneous eco-catalyst for the synthesis of imines among those reported to date. The Cu can be recovered from used Cu/HMPC by a simple HCl treatment. Versatility, heterogeneity and reusability of Cu/HMPC were tested. A possible mechanism has been proposed.

Tapioca cellulose based copper nanoparticles for chemoselective N-alkylation

Biomaterials as a support for catalysts are of prime importance. Tapioca root which is an abundant biopolymer source was used to synthesize cellulose supported bio-heterogeneous poly(hydroxamic acid) copper nanoparticles (CuN@PHA) and was characterized by Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV-Vis), field emission scanning electron microscopy (FESEM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma atomic emission spectroscopy (ICP-AES), transmission electron microscopy (TEM) analyses. The tapioca cellulose supported CuN@PHA (50 mol ppm) effectively catalyzed N-alkylation reaction of aliphatic amines with α,β-unsaturated compounds to give the corresponding alkylated products. High yields up to 95% were achieved for the converted products. The reusability of the cellulose supported nanoparticles was found to be excellent with no significant reduction of its catalytic activity over several cycles. The catalyst showed high catalytic activity having turnover number (TON) 18000 and turnover frequency (TOF) 2250 h-1.

Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts

Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.

A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite

Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]

Nickel(II) N-Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions

A variety of NiII complexes with a wide range of electronic and steric properties, bearing picolylimidazolidene ligands (a–g) and Cp (Cp = η5-C5H5; 2a–f) or Cp* (Cp* = η5-C5Me5; 3a, c, g) groups, have been synthesised and characterised by using NMR spectroscopy and single-crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations, which most likely involve a Ni0/NiII catalytic cycle. In particular, the new well-defined 2a, 2c, 3a and 3c complexes have demonstrated great efficiency and versatility towards Suzuki–Miyaura coupling reactions, hydroamination of activated olefins and C–S cross-coupling reactions of aryl halides and thiols under mild conditions.

Waste corn-cob cellulose supported bio-heterogeneous copper nanoparticles for aza-Michael reactions

Bio-heterogeneous poly(amidoxime) copper nanoparticles were prepared on the modified surface of waste corn-cob cellulose through a graft copolymerization process. The Cu-nanoparticles (0.05 mol% to 50 mol ppm) selectively promoted the aza-Michael reaction of aliphatic amines to give the corresponding alkylated products at room temperature in methanol. The supported nanoparticles were easy to recover and reused eight times without a significant loss of their activity.