492-85-3

Basic information

• Product Name: nicopholine
• Synonyms: nicopholine;3-(Morpholinocarbonyl)pyridine;4-(3-Pyridinylcarbonyl)morpholine;4-Nicotinoylmorpholine;morpholin-4-yl(pyridin-3-yl)methanone;morpholino(3-pyridyl)methanone
• CAS NO: 492-85-3
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• EINECS: 207-763-0
• Mol File: 492-85-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 365.6°Cat760mmHg
• Flash Point: 174.9°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: nicopholine(CAS DataBase Reference)
• NIST Chemistry Reference: nicopholine(492-85-3)
• EPA Substance Registry System: nicopholine(492-85-3)

Safety Data

• Hazardous Substances Data: 492-85-3(Hazardous Substances Data)

Usage

Uses

antitrypanosomal

InChI:InChI=1/C10H12N2O2/c13-10(9-2-1-3-11-8-9)12-4-6-14-7-5-12/h1-3,8H,4-7H2

Upstream product

• 59-67-6 nicotinic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 110-91-8 morpholine 
• 3099-50-1 3-trichloromethyl-pyridine 
• 626-55-1 3-Bromopyridine 
• 67-66-3 chloroform 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 15226-74-1 dicobalt octacarbonyl 
• 1120-90-7 3-iodopyridine 
• 201230-82-2 carbon monoxide 
• 100-55-0 3-hydroxymethylpyridin 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 7257-62-7 4-[(2-nitrophenyl)sulfanyl]morpholine 
• 78966-71-9 S-(2-nitrophenyl)-3-pyridinecarbothioate 

Downstream Products

• 91681-90-2 1-benzyl-3-morpholinocarbonylpyridinium bromide 
• 35091-00-0 4-[1-(3,4-dimethoxy-phenethyl)-piperidine-3-carbonyl]-morpholine 
• 35090-96-1 morpholino(piperidin-3-yl)methanone 
• 102165-55-9 4-[1-(3-phenyl-propyl)-piperidine-3-carbonyl]-morpholine 
• 111089-66-8 3-(morpholine-4-carbonyl)-1-phenethyl-pyridinium; bromide 

Relevant articles and documents

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Nickel-Catalyzed Amide Bond Formation from Methyl Esters

Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.

Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols

A Cu-catalyzed synthesis of amides from alcohols and secondary amines using the oxygen in air as the terminal oxidant has been developed. The methodology is operationally simple requiring no high pressure equipment or handling of pure oxygen. The commercially available, nonprecious metal catalyst, Cu(phen)Cl2, in conjunction with di-tert-butyl hydrazine dicarboxylate and an inorganic base provides a variety of benzamides in moderate to excellent yields. The pKa of amine conjugate acid and electronics of alcohol were shown to impact the selection of base for optimal reactivity. A mechanism consistent with the observed reactivity trends, KIE, and Hammett study is proposed.