2603-09-0

Usage

Chemical structure

A piperidine derivative with a carboxamide group and a 4-chlorophenyl substituent.

Pharmaceutical applications

Studied for its potential use as an analgesic agent.

Medicinal chemistry and drug discovery

Has potential applications in these fields.

Handling and management

Should be handled with caution to minimize risks to human health and the environment.

Upstream product

• 110-89-4 piperidine 
• 124255-71-6 1-(4-Chloro-phenyl)-3-[1-methoxy-1-phenyl-meth-(Z)-ylidene]-urea 
• 3768-56-7 1-(trimethylsilyl)piperidine 
• 104-12-1 p-chlorphenylisocyanate 
• 1885-81-0 p-chlorophenyl isocyanide 
• 201230-82-2 carbon monoxide 
• 106-47-8 4-chloro-aniline 
• 25290-48-6 1-(4-Chloro-phenyl)-3-[2,2-dimethyl-1-phenyl-prop-(E)-ylidene]-urea 
• 25290-58-8 1-Benzhydrylidene-3-(4-chloro-phenyl)-urea 
• 75461-60-8 N-Formyl-N-phenyl-N'-4-chlorophenylharnstoff 
• 57160-49-3 N-(4-chlorobenzoyl)-N'-(4-chlorophenyl)urea 

Downstream Products

• 1219-99-4 N,N'-bis(4-chlorophenyl)urea 

Relevant academic research and scientific papers

CaI2-Catalyzed direct transformation of: N -Alloc-, N -Troc-, and N -Cbz-protected amines to asymmetrical ureas

A novel and facile CaI2-catalyzed direct synthesis of asymmetrical ureas from N-Alloc-, N-Troc-, and N-Cbz-protected amines is developed. In this study, the efficient reaction of Alloc-, Troc-, and Cbz-carbamates with amines in the presence of catalytic CaI2 successfully generated various asymmetrical ureas. This catalytic synthetic procedure provided the desired ureas via reactions of these protected aromatic and aliphatic amines with various amines in high yields without side products. This suggests that novel direct synthesis of ureas from Alloc-, Troc-, and Cbz-carbamates can be a promising approach for the synthesis of useful ureas.

Rhodium-Catalyzed Oxidative Coupling Reaction of Isocyanides with Alcohols or Amines and Molecular Oxygen as Oxygen Source: Synthesis of Carbamates and Ureas

The first Rh-catalyzed aerobic oxidative coupling reaction of isocyanides with alcohols or amines has been developed. The reaction takes place under very mild conditions, by using air as the terminal oxidant and oxygen-atom source. It provides a simple, efficient, and general method for the construction of N-arylcarbamates and ureas in an atom-economic manner. Moreover, the new mechanism, involving α-diazocarbonyl compounds as carbene precursors and a RhI/RhIIIcatalytic cycle with oxygen, might open up new avenues in rhodium chemistry.

Pd(OAc)2-catalyzed carbonylation of amines

A phosphine-free catalytic system [Pd(OAc)2-Cu(OAc) 2-air] induced a substrate-specific carbonylation of amines in boiling toluene under CO gas (1 atm). Symmetrical N,N′-dialkylureas were obtained by the carbonylation of primary amines. N,N,N′-Trialkylureas were selectively formed by addition of a secondary amine to the above reaction vessel. Secondary amines did not give tetraalkylureas. However, dialkylamines with a phenyl group on their alkyl chains, such as N-monoalkylated benzylic amine or phenethylamine derivatives, underwent a direct aromatic carbonylation to afford five- or six-membered benzolactams. In the carbonylation, the chelation effect or steric repulsion between Pd(II) and the meta-substituent in the ortho-palladation and the ring sizes of cyclopalladation products that were formed prior to carbonylation were found to generate good site selectivity and increase the reaction rate. In contrast, carbonylation of ω- arylalkylamines with a hydroxyl group gave neither ureas nor benzolactams but instead produced 1,3-oxazolidinones smoothly. Hydrochlorides of amines also underwent carbonylation to afford the corresponding amides under the conditions used. This procedure made it possible to prepare ureas of amino acid esters and N-alkylcarbamates in practical yields.

REACTIONS OF ISOTHIOCYANATES AND ISOCYANATES WITH SOME SILYLATED NITROGEN-CONTAINING NUCLEOPHILES

Aryl isothiocyanates and arylisocyanates react with N,O-bis(trimethylsilyl)acetamide to give N-methyl-N'-arylthioureas and ureas.Also nucleophilic additions of other aprotic nucleophiles (e.g.N-trimethylsilylimidazole, N-trimethylsilylpiperidine and N-trimethylsilylmorpholine) to the N=C=X (X=O,S) group were investigated.

The reaction of imidates with isocyanates

Derivatives of isocyanates were prepared by reaction with imidates. Fragmentation reactions and behaviour in a simple biological test were examined.

N-Acyl- and N-Aryl-N'-alkylidenureas as Precursors of Isocyanates or Acylisocyanates

Derivatives of isocyanates or acylisocyanates were prepared by reactions with ketimines.Fragmentation reactions of the product were examined.

Reactions of N- or N'-Blocked N-acylureas with Amines

In order to make reactions of N-acylureas with amines more selective N- or N'-blocked derivatives were prepared.Their fragmentation was examined.