1016-50-8

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-phenylethyl)pyrrolidine-2,5-dione is used as a core structure for the synthesis of various pharmaceutical compounds due to its potential biological activities and versatility in medicinal chemistry.
Used in Neurological Disorders Treatment:
1-(2-phenylethyl)pyrrolidine-2,5-dione is used as a potential therapeutic agent for the treatment of neurological disorders, leveraging its anticonvulsant properties to manage seizure activity.
Used in Psychiatric Conditions Management:
1-(2-phenylethyl)pyrrolidine-2,5-dione is used as a potential agent in the management of psychiatric conditions, owing to its psychotropic and sedative effects, which may help in alleviating symptoms associated with such conditions.
Used in Drug Development Research:
1-(2-phenylethyl)pyrrolidine-2,5-dione is used as a subject of research in drug development, as its exploration for potential applications continues to expand, offering new possibilities for the treatment of various conditions.

Upstream product

• 123-91-1 1,4-dioxane 
• 110-15-6 succinic acid 
• 64-04-0 phenethylamine 
• 123-25-1 succinic acid diethyl ester 
• 123-56-8 Succinimide 
• 103-63-9 1-phenyl-2-bromoethane 
• 128-09-6 N-chloro-succinimide 
• 501-52-0 3-Phenylpropionic acid 
• 516-12-1 N-iodo-succinimide 
• 110-63-4 Butane-1,4-diol 
• 4796-01-4 N-2-phenylethylmaleamic acid 
• 6943-90-4 N-phenethylmaleimide 
• 108-30-5 succinic acid anhydride 
• 1083-55-2 N-(2-phenylethyl)succinamic acid 

Downstream Products

• 6908-75-4 N-(2-phenylethyl)pyrrolidine 
• 861035-95-2 1-(2-cyclohexyl-ethyl)-pyrrolidin-2-one 
• 856353-96-3 1-(2′-cyclohexylethyl)pyrrolidine-2,5-dione 
• 191864-36-5 N-<2-(4-nitrophenyl)ethyl>succinimide 
• 123-56-8 Succinimide 
• 81416-16-2 6-phenylhexahydroazepine-2,5-dione 
• 66951-59-5 N-(4-amino-phenethyl)-succinimide 
• 857753-98-1 N-{4-[bis-(2-hydroxy-ethyl)-amino]-phenethyl}-succinimide 
• 860428-66-6 N-{4-[bis-(2-chloro-ethyl)-amino]-phenethyl}-succinimide 
• 58880-18-5 4-[bis-(2-chloro-ethyl)-amino]-phenethylamine 
• 7530-17-8 1-(2-cyclohexyl-ethyl)-pyrrolidine 
• 39662-49-2 5-hydroxy-1-phenethyl-pyrrolidin-2-one 

Relevant academic research and scientific papers

Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts

We describe the synthesis of tetrahydroisoquinolines and tetrahydroisoquinolinium salts together with their pharmacological properties at various nicotinic acetylcholine receptors. In general, the compounds were α4β2 nAChR antagonists, with the tetrahydroisoquinolinium salts being more potent than the parent tetrahydroisoquinoline derivatives. The most potent α4β2 antagonist, 6c, exhibited submicromolar binding Ki and functional IC50 values and high selectivity for this receptor over the α4β4 and α3β4 nAChRs. Whereas the (S)-6c enantiomer was essentially inactive at α4β2, (R)-6c was a slightly more potent α4β2 antagonist than the reference β2-nAChR antagonist DHβη. The observation that the α4β2 activity resided exclusively in the (R)-enantiomer was in full agreement with docking studies. Several of tetrahydroisoquinolinium salts also displayed agonist activity at the α7 nAChR. Preliminary in vivo evaluation revealed antidepressant-like effects of both (R)-5c and (R)-6c in the mouse forced swim test, supporting the therapeutic potential of α4β2 nAChR antagonists for this indication.

Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst

In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.

Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst

Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.

Synthesis of Cyclic Imides by Acceptorless Dehydrogenative Coupling of Diols and Amines Catalyzed by a Manganese Pincer Complex

The first example of base-metal-catalyzed dehydrogenative coupling of diols and amines to form cyclic imides is reported. The reaction is catalyzed by a pincer complex of the earth abundant manganese and forms hydrogen gas as the sole byproduct, making the overall process atom economical and environmentally benign.

MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS

The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

PROCESS FOR PRODUCING N-ALKYL-IMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide a process for producing an N-alkyl-imide compound in which an N-alkyl-imide compound can be produced by using an inexpensive and widely distributed aliphatic carboxylic acid compound and an N-halogenated imide compound as a raw material and carrying out the reaction in one-pot under a mild condition. SOLUTION: The process for producing an N-alkyl-imide compound is characterized to include: a first step of reacting a mixture of an aliphatic carboxylic acid compound having an aliphatic group, an N-halogenated imide compound and iodine; and a second step of reacting the mixture after the first step and a base. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

One-Pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccin-imides with NIS and NCS/NaI

Primary aliphatic carboxylic acids were treated with N-iodosuccinimide (NIS) in 1,2-dichloroethane to form the corresponding alkyl iodides under warming conditions. Based on these results, those aliphatic carboxylic acids were treated with NIS, followed by the reaction with K2CO3to give the corresponding N-alkylsuccinimides in good yields in one pot. Moreover, those aliphatic carboxylic acids were treated with N-chlorosuccinimide (NCS) and NaI, followed by the reaction with K2CO3to provide the corresponding N-alkylsuccinimides in good to moderate yields in one pot. By using the present method, successive treatment of primary aliphatic carboxylic acids (10 mmol) with NIS, K2CO3, and then hydrazine provided the corresponding decarboxylated primary amines in good yield.

Synthesis of condensed tetrahydroisoquinoline class of alkaloids by employing TfOH-mediated imide carbonyl activation

Isoquinoline-based polycyclic lactams such as isoindoloisoquinolinones, pyrroloisoquinolinones, and benzo[a]quinolizinones were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. By employing this simple method, the isoquinoline alkaloids crispine A, trolline/oleracein E, and erythrinarbine were successfully synthesized in racemic form. The reaction of unsymmetrical N-phenethylphthalimides with TfOH displayed excellent regioselectivity, which was rationalized by DFT calculations.

Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction

The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.

PROCESS OF FORMING A CYCLIC IMIDE

A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.