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Usage

Uses

Used in Pharmaceutical Development:
1-(3-Phenylpropyl)piperazine is used as a drug candidate for the treatment of various psychiatric and neurological disorders due to its demonstrated affinity for specific neurotransmitter receptors in the brain, which may contribute to its therapeutic effects.
Used in Chemical Synthesis:
1-(3-Phenylpropyl)piperazine is utilized as a precursor in the synthesis of other organic compounds, highlighting its versatility and importance in the field of organic chemistry.
Used in Research Compounds:
As a member of the piperazine derivatives class, 1-(3-Phenylpropyl)piperazine is employed as a research compound to explore its potential applications and mechanisms of action in various medical and scientific contexts.

Upstream product

• 637-59-2 1-Bromo-3-phenylpropane 
• 7542-23-6 piperazine hydrochloride 
• 117132-90-8 1-(3-phenylpropionyl)piperazine 
• 59698-38-3 4-(3-phenyl-propyl)-piperazine-1-carboxylic acid ethyl ester 
• 110-85-0 piperazine 
• 104-52-9 phenylpropyl chloride 
• 18903-01-0 trans-1-cinnamylpiperazine 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 

Downstream Products

• 132019-73-9 N-(5,11-Dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-4-[4-(3-phenyl-propyl)-piperazin-1-yl]-butyramide 
• 198895-71-5 1-[N-(tert-butoxycarbonyl)aminoacetyl]-4-(3-phenylpropan-1-yl)piperazine 
• 219659-36-6 {4-Oxo-4-[4-(3-phenyl-propyl)-piperazin-1-yl]-butyl}-carbamic acid tert-butyl ester 
• 219659-35-5 {3-Oxo-3-[4-(3-phenyl-propyl)-piperazin-1-yl]-propyl}-carbamic acid tert-butyl ester 
• 219659-15-1 YZ 155-2 
• 219659-13-9 2-(2-Nitro-phenyl)-1-[4-(3-phenyl-propyl)-piperazin-1-yl]-ethanone 
• 219659-14-0 2-(3-Nitro-phenyl)-1-[4-(3-phenyl-propyl)-piperazin-1-yl]-ethanone 
• 219659-17-3 2-(3-Methoxy-phenyl)-1-[4-(3-phenyl-propyl)-piperazin-1-yl]-ethanone 

Relevant academic research and scientific papers

Synthesis of formamides containing unsaturated groups by: N -formylation of amines using CO2 with H2

Formamides have wide applications in the industry and have been synthesized using CO2 as a carbon source and H2 as a reducing agent. However, previous systems required a noble catalyst and high temperature to achieve high efficiency, and the substrate scope was mostly limited to saturated amines. The selective N-formylation of amines containing unsaturated groups using CO2 and H2 is challenging because the efficient catalysts for the N-formylation are usually very active for hydrogenation of the unsaturated groups. Herein, we achieved for the first time a selective and efficient N-formylation of amines containing unsaturated groups using CO2 and H2 with a Cu(OAc)2-4-dimethylaminopyridine (DMAP) catalytic system. The substrates were converted to the desired formamides, while the unsaturated groups, such as the carbonyl group, the CC bond, CN bond and the ester group remained. The main reason for the excellent selectivity of the Cu(OAc)2-DMAP catalytic system was that it was very active for the N-formylation reaction, but was not active for the hydrogenation of the unsaturated groups.

Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors

Monoamine transporters regulate the concentration of monoamine neurotransmitters, which are essential for vital physiological processes, and their dysfunction can cause several central nervous system diseases. Monoamine transporters currently appear to be the potential target in the management of these disorders. In this study, homologation and bioisosterism techniques have been used in the designing of new 1,4-disubstituted piperazines and piperidines. These derivatives were synthesized and evaluated as potential triple reuptake inhibitors for studying the structure-activity relationships. The most advanced compound, 1-(4-(5-benzhydryl-1H-tetrazol-1-yl)butyl)-4-(3-phenylpropyl)piperazine (2i), was able to inhibit monoamine neurotransmitter reuptake in an in vitro test (IC50?=?158.7?nM for 5-HT, 99?nM for NE and 97.5?nM for DA). These novel potent triple reuptake inhibitor-based 1,4-disubstituted piperazine and piperidine scaffolds deserve further systematic optimization and pharmacological evaluation.

Rhodium-Catalyzed Bis-Hydroaminomethylation of Linear Aliphatic Alkenes with Piperazine

An efficient protocol was developed to prepare a series of dialkylpiperazines via Rh-catalyzed bis-hydroaminomethylation of linear aliphatic alkenes with piperazine. The well-known Rh/Biphephos catalytic system was applied, yielding the desired dialkylpiperazines within six tandem catalytic steps, already at low catalyst loadings of 0.1 mol%. For the model alkene 1-octene, good yields and linearities of 80% and 77:23, respectively, were achieved under optimized conditions. Influences on the catalytic system regarding n/iso ratio, possible side reactions and the reaction path are discussed on the basis of yield vs. time plots and parameter optimization. With the developed general protocol, other linear, functionalized and branched substrates were effectively transformed to the corresponding linear N,N-disubstituted piperazines.

Synthesis and evaluation of novel 18F-labeled spirocyclic piperidine derivatives as σ1 receptor ligands for positron emission tomography imaging

A series of spirocyclic piperidine derivatives were designed and synthesized as σ1 receptor ligands. In vitro competition binding assays showed that 1′-(4-(2-fluoroethoxy)benzyl)-3H-spiro[2- benzofuran-1,4′-piperidine] (19) possessed high σ1 receptor affinity (Ki = 0.79 nM) and excellent σ1/ σ2 subtype selectivity (350-fold) as well as high σ1/VAChT selectivity (799-fold). The radiolabeled compound [18F]19 was synthesized by substitution of the tosylate precursor 24 with [18F]fluoride, with an isolated radiochemical yield of 35-60%, a radiochemical purity of >99%, and a specific activity of 30-55 GBq/μmol. Biodistribution studies in imprinting control region mice indicated that [ 18F]19 displayed excellent initial brain uptake and slow washout. Ex vivo autoradiography in Sprague-Dawley rats demonstrated high accumulation of the radiotracer in brain areas known to express high levels of σ1 receptors. Micro positron emission tomography imaging and blocking studies confirmed the specific binding of [18F]19 to σ1 receptors in vivo.

Solid-Phase Polyamine Synthesis Using Piperazine and Piperidine Building Blocks

(Equation presented) Polyamines containing piperidine and piperazine moieties have been synthesized on solid support using SN2 alkylation of resin-bound secondary amines with 2-nitrobenzenesulfonates (nosylates). The effect of solvent on this a

Synthesis and preliminary pharmacological evaluation of 4′-arylalkyl analogues of clozapine. II. Effect of the nature and length of the linker

We report the synthesis of a second generation of tricyclic analogues of clozapine, investigating the length and nature of the chain between an ionizable nitrogen atom at physiological pH and the introduced aryl moiety. The chemistry, structural characterization, and pharmacological evaluation of this series of 4′-arylalkyl analogues of clozapine are described. Preliminary findings on the effects on activity of the nature and length of the linker, degree of unsaturation, and type of aryl moiety on blockade of dopamine D4 and serotonin 5-HT2A receptors are discussed and animal behavioural data for key compounds presented.

Scale-up synthesis of the dopamine uptake inhibitor GBR-12909

1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.

Characterization of novel N,N'-disubstituted piperazines as σ receptor ligands

σ Receptors have been the focus of extensive studies because of their potential functional role in several important physiological and biochemical processes. To further evaluate the properties of σ receptors, especially σ- 1 and σ-2 subtypes, we have synt

Azolyl-cyclic amine derivates with immunomodulatory activity

A compound of the formula (I), STR1 as defined in the specification, having immunomodulatory activity, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising the compound, and processes to make and to use the compound are described.

Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as σ site-selective ligands

Starting from a random screening showing that 2-[(4- benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.