3389-53-5

Basic information

• Product Name: Pyrrolidine, 1-(phenylacetyl)-
• Synonyms: 1-phenylacetylpyrrolidine;phenylacetylpyrrolidine;phenylacetic pyrrolidine;1-phenylacetyl pyrolidine;2-phenyl-1-pyrrolidin-1-yl-ethanone
• CAS NO: 3389-53-5
• Molecular Formula: C12H15NO
• Molecular Weight: 189.257
• Mol File: 3389-53-5.mol
• Article Data: 59

Chemical Properties

• Melting Point: 146-147 °C
• Boiling Point: 172-178 °C(Press: 3 Torr)
• Density: 1.102±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Pyrrolidine, 1-(phenylacetyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 1-(phenylacetyl)-(3389-53-5)
• EPA Substance Registry System: Pyrrolidine, 1-(phenylacetyl)-(3389-53-5)

Safety Data

• Hazardous Substances Data: 3389-53-5(Hazardous Substances Data)

Usage

General Description

Pyrrolidine, 1-(phenylacetyl)-, also known as Phenylpiracetam, is a synthetic chemical compound derived from the neurotransmitter gamma-aminobutyric acid (GABA). It belongs to the racetam class of compounds and is known for its potential nootropic and cognitive enhancing effects. Phenylpiracetam has been studied for its potential to improve memory and cognitive function, as well as its stimulant-like properties. It is also believed to have potential anti-amnesic, anticonvulsant, and anxiolytic effects. However, more research is needed to fully understand its mechanisms of action and potential therapeutic uses. Phenylpiracetam is considered a stimulant and is banned by the World Anti-Doping Agency (WADA) for use in competitive sports.

Upstream product

• 123-75-1 pyrrolidine 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 1483-82-5 phenylethynyl chloride 
• 101-41-7 benzeneacetic acid methyl ester 
• 30516-21-3 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylethan-1-one 
• 2700-22-3 Benzylidenemalononitrile 
• 100-52-7 benzaldehyde 
• 1867-37-4 Benzylmalononitrile 
• 3760-54-1 1-pyrrolidinecarboxaldehyde 
• 103-81-1 Benzeneacetamide 
• 1555-80-2 phenylacetic anhydride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 1532548-78-9 1-(prop-2-ene-1-sulfinyl)pyrrolidine 

Downstream Products

• 93999-50-9 1-(4-diethylamino-2-phenyl-butyryl)-pyrrolidine 
• 1449216-48-1 2-(4-(tert-butyl)phenyl)-2-phenyl-1-(pyrrolidin-1-yl)ethanone 
• 103383-80-8 1-phenyl-2-(pyrrolidin-1-yl)ethane-1,2-dione 
• 1408382-01-3 7-methoxy-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 

Relevant articles and documents

Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines

A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is

Regioselective synthesis of: Ortho -iodobiphenylboronic acid derivatives: A superior catalyst for carboxylic acid activation

An efficient and versatile synthesis of ortho-iodobiphenylboronic acids via the highly regioselective metal-iodine exchange (MIE) of 2,3-diiodobiphenyls is reported. The site-selectivity is very much controlled by the size of the biphenyl fragment, providing only the terminal arylboronic acid derivatives in excellent site-selectivity. The nature of the substituents (R1 and R2) on the biphenyls is found to have an influence on the reactivity but not on the regioselectivity. The best reactivity and the highest isolated yields were furnished with products bearing electron-donating groups. The synthesized derivatives were also tested for in vitro antimicrobial activity against four strains of bacteria and one fungal strain. This revealed that (2-iodo-4′-isopropyl-[1,1′-biphenyl]-3-yl)boronic acid 6A and (3-(benzo[d][1,3]dioxol-5-yl)-2-iodo-5-methoxyphenyl)boronic acid 22A possess the most potent antibacterial and antifungal activity with MICs of 0.10 and 0.3 mg mL-1 for B. cereus and C. albicans respectively. The catalytic activity was also examined towards an amidation reaction at ambient temperature and this revealed a new optimal catalyst, (2-iodo-4′,5-dimethoxy-[1,1′-biphenyl]-3-yl)boronic acid 19A providing a remarkable increase in the amide yields, including α-aminoacids. This work discloses a protocol for the first synthesis of hitherto unknown ortho-iodobiphenylboronic acid derivatives that is scalable, and general in scope, where no chromatographic purification is necessary and the products are indeed potential organocatalysts.

Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.