63921-21-1

Basic information

• Product Name: 1-Phenylpiperidin-3-amine
• Synonyms: 1-PHENYLPIPERIDIN-3-AMINE;1-Phenyl-3-piperidinamine
• CAS NO: 63921-21-1
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.26
• Mol File: 63921-21-1.mol

Chemical Properties

• Boiling Point: 295 °C
• Flash Point: 117 °C
• Appearance: /
• Density: 1.041
• CAS DataBase Reference: 1-Phenylpiperidin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylpiperidin-3-amine(63921-21-1)
• EPA Substance Registry System: 1-Phenylpiperidin-3-amine(63921-21-1)

Safety Data

• Hazardous Substances Data: 63921-21-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenylpiperidin-3-amine is used as a psychoactive drug for its potential therapeutic effects on conditions such as depression and attention deficit hyperactivity disorder (ADHD), due to its action as a releasing agent for dopamine and norepinephrine, which can increase energy and improve mood.
Used in Research and Development:
1-Phenylpiperidin-3-amine is utilized in scientific research to study the effects of neurotransmitter release and the mechanisms of psychoactive substances, contributing to the development of new treatments for neurological and psychiatric disorders.

Upstream product

• 54012-73-6 3-aminopiperidine 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 108-90-7 chlorobenzene 
• 184637-48-7 t-butyl piperidin-3-ylcarbamate 
• 127294-75-1 3-amino-piperidine dihydrochloride 

Relevant articles and documents

BENZAZEPINE DICARBOXAMIDE COMPOUNDS WITH SECONDARY AMIDE FUNCTION

This invention relates to new benzazepine dicarboxamide compounds of the formula (I) wherein R1 to R4 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.

Palladium-mediated N-arylation of heterocyclic diamines: Insights into the origin of an unusual chemoselectivity

The chemoselectivity of the palladium-mediated reaction of bromobenzene with various heterocyclic diamines was studied. Whatever the ligand used, 3-aminopyrrolidine underwent arylation of the secondary amine function (> 82%), whereas the more flexible 3-aminoazepinine was arylated on its primary function (>70%). The ratio "arylation of primary amine versus arylation of secondary amine" of 3-aminopiperidine with bromobenzene varied from 90:10 (BINAP, electron-enriched and hindered biphenyls L2 or L3) to 32:68 with the Josiphos-type ligand L10. The same trend was observed when 4-aminopiperidine was used (82:18 with L2 and 17:83 with L10). This selectivity can be tuned by the choice of aryl halide partners having different steric and electronic properties. A cooperative effect of both nitrogens of diamines during the reaction was deduced from competitive experiments. Finally, 13C and 31P NMR experiments, carried out with 3-aminopyrrolidine at room temperature, support a fast coordination of the primary amine to the metal. Indeed, a palladium complex resulting from the unusual displacement of one phosphane group of the intermediate ArPdX(BINAP) by the primary amino group was characterized.

Palladium-mediated arylation of 3-aminopiperidines and 3-aminopyrrolidines

This paper describes the palladium-catalyzed arylation of 1-substituted 3-aminopyrrolidines or piperidines. Palladium(0) (1-2 mol %) in conjunction with "Buchwald's ligand" [2-(dimethylamino)-2′- (dicyclohexylphosphine)biphenyll was shown to be the catalyst of choice for the coupling with aryl bromides or chlorides. When bromobenzene was used, a strong temperature effect was noticed. Whereas no reaction occurred at 100 °C, yields higher than 85% were obtained at 130 °C for each substrate. Such an effect was not observed when diphosphines were used. Whereas Xantphos and, to a lesser extent BINAP, were moderately efficient in the coupling of all diamines, the palladium-mediated arylation in the presence of monophosphines was strongly dependent on the substrate. The results suggest the participation of both nitrogens of the aminoheterocycle in the reactive intermediate. This participation could also account for the highly selective arylation of the endocyclic nitrogen of unsubstituted 3-aminopyrrolidine or piperidine. Optimal conditions were found for the arylation using 2- or 4-substituted electron-poor or enriched aryl halides.