2589-19-7

Usage

Classification

Piperazine derivative

Uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Psychoactive properties

Yes

Recreational drug use

Sometimes

Regulation

Regulated in some countries

Potential medical applications

Treatment of depression, anxiety, and other psychiatric disorders

Regulatory approval

Not approved by regulatory authorities

Controlled substance

Considered controlled in some jurisdictions

Health and safety risks

May pose risks, should be handled with caution

Upstream product

• 110-89-4 piperidine 
• 201230-82-2 carbon monoxide 
• 106-49-0 p-toluidine 
• 86065-10-3 O-allyl-N-(4-methylphenyl)carbamate 
• 124255-72-7 1-[1-Methoxy-1-phenyl-meth-(Z)-ylidene]-3-p-tolyl-urea 
• 33275-26-2 N-(4-methylphenyl)-O-phenyl carbamate 

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.

Synthesis of unsymmetrical ureas by sulfur-assisted carbonylation with carbon monoxide and oxidation with molecular oxygen under mild conditions

With ambient pressure of carbon monoxide and oxygen at room temperature, N,N-dialkyl-N′-arylureas were selectively accessible from secondary amines, aromatic amines, and sulfur in good to excellent yields. For example, N-butyl-N-methyl-N′-(3,4-dichlorophenyl)urea, which is used as a herbicide (neburon), was afforded successfully from butylmethylamine (2 equiv), 3,4-dichloroaniline (1 equiv) and sulfur (1 equiv) in 79% (21.8 g) yield using carbon monoxide (0.1 MPa) and oxygen (0.1 MPa) at 20°C in DMF. Georg Thieme Verlag Stuttgart.

Phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as carbonyl source: Facile and selective synthesis of carbamates and ureas under mild conditions

The selective syntheses of carbamates, symmetric -ureas, and unsymmetrical ureas have been accomplished by the -reaction of amines with phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as a carbonyl source under mild conditions. It is noteworthy that this process is mild, economic, and convenient.

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.