24438-88-8

Usage

Uses

Used in Pharmaceutical Industry:
3-(PYRROLIDIN-1-YL)PROPANAMIDE is used as a precursor in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Medicinal Chemistry:
3-(PYRROLIDIN-1-YL)PROPANAMIDE is used as a building block in medicinal chemistry for its potential to form biologically active molecules, aiding in drug discovery and the advancement of therapeutic agents.
Used in Organic Chemistry:
3-(PYRROLIDIN-1-YL)PROPANAMIDE is used as a versatile chemical intermediate in organic chemistry for its potential to participate in a wide range of chemical reactions, leading to the creation of diverse organic compounds.

InChI:InChI=1/C7H14N2O/c8-7(10)3-6-9-4-1-2-5-9/h1-6H2,(H2,8,10)

Upstream product

• 123-75-1 pyrrolidine 
• 6320-96-3 3-bromopropanamide 
• 79-06-1 2-propenamide 

Relevant academic research and scientific papers

Efficient, simple preparation of 1,3-diamine derivatives through addition of acrylamides with secondary amines

Reaction of acrylamides with secondary amines results in the formation of β-amino-propionamide through the addition reaction of N-H bond of amines across the double bond of acrylamides in the good to excellent yield. The structure of 2-methyl-3-(1-piperidinyl)-propionamide has been determined by X-ray analysis. Copyright Taylor & Francis, Inc.

Catalysis of nucleophilic addition of pyrrolidine to 2-(5H)-furanone through chromenone cleft-type receptors

Several H-bonding receptors are shown to significantly catalyze the nucleophilic addition of pyrrolidine to 2-(5H)-furanone to a significant extent. Combination of these receptors with a sulfonamide group affords a further increase in the catalytic effect of these molecules.

Understanding water mediated proton migration in conversion of π-bond in olefinic carbon atoms into C–N bond to form β-amino adducts

The aza-Michael reactions with a variety of substrates were conducted in water affording the quantitative yields without any external catalyst, which is contrary to that published in literature. A more rational approach to analyze this problem was by conducting this conspicuous reaction with a variety of substrates in water and the results were analyzed using advanced theoretical calculations. Our investigation on the role of water in the reaction proposed a mechanism wherein water plays dual role both as medium as well as catalyst to facilitate the C–N bond formation using powerful tool in its armory, the “H-bonding”. Reactions were conducted in the absence of an external catalyst or co-solvents and, hence, are a greener approach in organic synthesis. The reactions of 15 examples were conducted with a variety of substrates to afford the addition products in the range of 70–95% yield. Theoretical studies on the transition state analysis suggested that it was the assistance of water, through H-bonding, that facilitated the conjugate addition of amine and proton transfer from ammonium ion, which could happen through two equally possible pathways.

Michael addition reaction catalyzed by imidazolium chloride to protect amino groups and construct medium ring heterocycles

An effective approach for amino protection and construction of a seven-membered ring has been developed. The method uses imidazolium chloride to carry out the Michael addition reaction at low temperatures and perform amino deprotection or construction of a seven-membered ring at high temperatures.

Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts

Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.

[CH3COO]: Efficient and recyclable catalyst for aza-Michael addition of α, β-unsaturated compounds and amines under solvent-free conditions

The recyclable ionic liquid [ADPQ][CH3COO] has been used as catalyst for aza-Michael addition of amines to α, β-unsaturated compounds to produce β-amino compounds. The reactions were complete in a few hours with high yields. The ionic liquid can be recycled and reused six times without noticeable decrease of catalytic activity.

DABCO-based ionic liquids: Recyclable catalysts for aza-michael addition of α,β-unsaturated amides under solvent-free conditions

An array of novel 1,4-diazobicyclo[2.2.2]octane (DABCO) based ionic liquids were developed and used as recyclable catalysts for the aza-Michael addition at room temperature without any organic solvent. [DABCO-PDO][OAc] was found to be the most efficient catalyst, and the amount of catalyst was only 10 mol %. Various amines reacted with a wide range of α,β-unsaturated amides, smoothly affording target products in good to excellent yields within hours. Moreover, the catalyst could be reused up to eight times, still maintaining a high catalytic activity. Finally, a plausible mechanism was proposed. FTIR and computational chemistry were used to verify the catalytic mechanism.

Ionic tagged DABCO grafted on magnetic nanoparticles: A water-compatible catalyst for the aqueous aza-Michael addition of amines to α,β- unsaturated amides

Ionic tagged 1,4-Diazabicyclo[2.2.2]octane (DABCO) grafted on magnetic nanoparticles (MNPs) was prepared and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), vibrating sample magnetometry (VSM) and thermal gravimetric analysis (TGA). The resulting magnetic solid supported DABCO catalyst with an ionic moiety was efficient for aza-Michael addition of aliphatic amines to various α,β-unsaturated amides in water at room temperature, affording the desired products in good to excellent yields. Gratifyingly, the catalyst could be readily recovered by an external magnet and reused ten times without any significant loss of activity. The Royal Society of Chemistry 2014.

Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes

Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.

An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls

A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.