13125-62-7

Upstream product

• 86-73-7 9H-fluorene 
• 857937-01-0 2-ethylamino-4-phenyl-butyric acid 
• 69375-96-8 cinnamyliden-ethyl-amine 
• 75-04-7 ethylamine 
• 104-52-9 phenylpropyl chloride 
• 557-66-4 ethanamine hydrochloride 
• 104-55-2 3-phenyl-propenal 
• 645-45-4 hydrocinnamic acid chloride 
• 2038-57-5 3-Phenylpropan-1-amine 
• 75-07-0 acetaldehyde 
• 637-59-2 1-Bromo-3-phenylpropane 
• 122-97-4 3-Phenyl-1-propanol 
• 501-52-0 3-Phenylpropionic acid 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 802902-79-0 1-(N-ethyl-(3-phenyl)propylamino)octan-3-one 
• 690211-89-3 ethyl 3-[Ethyl-(3-Phenylpropyl)Amino]Propionate 
• 150-59-4 alverine 
• 1263429-53-3 N-ethyl-3-phenylpropyl-1-sulfamoyl azide 
• 1263429-67-9 C₁₁H₁₆N₂O₂S 
• 128667-60-7 6-{3-[Ethyl-(3-phenyl-propyl)-amino]-2-hydroxy-propoxy}-1H-quinolin-2-one 

Relevant academic research and scientific papers

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

The cubane paradigm in bioactive molecule discovery: Further scope, limitations and the cyclooctatetraene complement

The cubane phenyl ring bioisostere paradigm was further explored in an extensive study covering a wide range of pharmaceutical and agrochemical templates, which included antibiotics (cefaclor, penicillin G) and antihistamine (diphenhydramine), a smooth muscle relaxant (alverine), an anaesthetic (ketamine), an agrochemical instecticide (triflumuron), an antiparasitic (benznidazole) and an anticancer agent (tamibarotene). This investigation highlights the scope and limitations of incorporating cubane into bioactive molecule discovery, both in terms of synthetic compatibility and physical property matching. Cubane maintained bioisosterism in the case of the Chagas disease antiparasitic benznidazole, although it was less active in the case of the anticancer agent (tamibarotenne). Application of the cyclooctatetraene (COT) (bio)motif complement was found to optimize benznidazole relative to the benzene parent, and augmented anticancer activity relative to the cubane analogue in the case of tamibarotene. Like all bioisosteres, scaffolds and biomotifs, however, there are limitations (e.g. synthetic implementation), and these have been specifically highlighted herein using failed examples. A summary of all templates prepared to date by our group that were biologically evaluated strongly supports the concept that cubane is a valuable tool in bioactive molecule discovery and COT is a viable complement.

Purifying method of N-ethyl-3-phenylpropylamine

The invention relates to a purifying method of N-ethyl-3-phenylpropylamine, and belongs to purifying method of compounds. A N-ethyl-3-phenylpropylamine sample with the lower purity is dissolved in a water insoluble organic solvent, the organic phase is extracted for 1-5 times by a water solution with the appropriate pH value, the aqueous phase is combined, alkali or an alkaline solution is added,the pH value is conditioned, the aqueous phase is extracted by the water insoluble organic solvent, the organic phase is combined, drying and filtration are conducted, and the solvent is dried out through decompression. The purifying method has the advantages that the purifying effect is good, the result is stable and reliable, thus the higher and higher quality requirement of the pharmacy industry for the midbody can be better satisfied, and the yield is high and can be as high as 80% or above. Production and operation are safer and more convenient, and the purifying method is suitable for large-scale production.

Preparation method of N-ethyl-3-phenylpropylamine

The invention relates to a preparation method of N-ethyl-3-phenylpropylamine, and belongs to a preparation method of a compound. The preparation method comprises the following steps: dropwise adding 3-hydrocinnamaldehyde into an alcohol solution of ethyla

Method for reducing residues of N-ethyl-3-phenylpropylamine in alverine

The invention relates to a method for reducing residues of N-ethyl-3-phenylpropylamine in alverine, and belongs to an impurity removal method of compounds. The method comprises the following steps: dissolving an intermediate alverine crude product containing impurity N-ethyl-3-phenylpropylamine into a water-insoluble organic solvent, extracting an organic layer by using an aqueous solution with appropriate pH and discarding a water layer; drying and filtering the organic layer, decompressing and evaporating the solvent to dryness. According to the method disclosed by the invention, a clear, simple and reliable solution to the residues of the N-ethyl-3-phenylpropylamine in the intermediate alverine is provided for the first time, so that the subsequently produced crude drug citric acid alverine has higher quality and the residue amount does not exceed 0.15 percent. The method has the advantages of simplicity, feasibility, low cost, few wastes and suitability for industrial popularization.

The ruthenium-catalyzed reduction and reductive N-alkylation of secondary amides with hydrosilanes: Practical synthesis of secondary and tertiary amines by judicious choice of hydrosilanes

(Chemical Equation Presented) A triruthenium cluster, (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7 (1) catalyzes the reaction of secondary amides with hydrosilanes, yielding a mixture of secondary amines, tertiary amines, and silyl enamines. Production of secondary amines with complete selectivity is achieved by the use of higher concentration of the catalyst (3 mol %) and the use of bifunctional hydrosilanes such as 1,1,3,3-tetramethyldisiloxane. Acidic workup of the reaction mixture affords the corresponding ammonium salts, which can be treated with a base, providing a facile method for isolation of secondary amines with high purity. In contrast, tertiary amines are formed with high selectivity by using lower concentration of the catalyst (1 mol %) and polymeric hydrosiloxanes (PMHS) as reducing agent. Reduction with PMHS encapsulates the ruthenium catalyst and organic byproducts to the insoluble silicone resin. The two reaction manifolds are applicable to various secondary amides and are practical in that the procedures provide the desired secondary or tertiary amine as a single product. The product contaminated with only minimal amounts of ruthenium and silicon residues. On the basis of the products and observed side products as well as NMR studies a mechanistic scenario for the reaction is also described.

Amines, uses thereof

The present invention relates to novel secondary or tertiary amines useful for smoothing wrinkles and fine lines, in particular expression wrinkles and fine lines.

Dopamine autoreceptor agonists as potential antipsychotics. 2. (Aminoalkoxy)-4H-1-benzopyran-4-ones

The synthesis and pharmacological properties of a novel type of [(arylpiperazinyl)alkoxy]-4H-1-benzopyran-4-ones with dopaminergic activity are described. The nature of the arylpiperazine (AP) moiety determines the dopamine (DA) agonist/antagonist character of this series of compounds; when the aryl portion of the AP is unsubstituted the compounds appear to be DA autoreceptor agonists while substituted aryl groups seem to impart DA antagonist activity. A heterocyclic piperazine, 7-[3-[4-(2-pyridinyl)-1-piperazinyl]propoxy]-4H-1-benzopyran-4-one (31, PD 119819) has been identified as an extremely selective DA autoreceptor agonist in tests that include [3H]haloperiodol binding, inhibition of spontaneous locomotor activity, inhibition of brain DA synthesis, inhibition of brain DA neuronal firing, stereotypy assessment, and reversal of 6-hydroxydopamine (6-OHDA) induced akinesia in rats. In addition, 31 possesses good oral activity in the Sidman avoidance test in squirrel monkeys, a predictor of clinical antipsychotic efficacy. In another primate model, 31 has been found to lack the liability for extrapyramidal side effects observed with currently available antipsychotic drugs.

Central cholinergic agents. I. Potent acetylcholinesterase inhibitors, 2-[ω-[N-alkyl-N-(ω-phenylalkyl)amino]alkyl]-1H-isoindole-1,3(2H)-dion es, based on a new hypothesis of the enzyme's active site

It has been suggested that the active site of acetylcholinesterase contains a hydrophobic binding site (HBS-1), which is closely adjacent to both the anionic and the esteratic sites. In this paper, we assumed that there exists another hydrophobic binding site (HBS-2), some distance removed from the anionic site. On this assumption, a new working hypothesis was proposed for the design of acetylcholinesterase inhibitors. A series of 2-[ω-[N-alkyl-N-(ω-phenylalkyl)amino]alkyl]-1H-isoindole-1,3(2H)-dion es was designed based on this hypothesis and tested for its inhibitory activities on acetylcholinesterase. Some in this series were revealed to be more potent than physostigmine. Optimum activity was found to be associated with a five carbon chain length separating the benzylamino group from the 1H-isoindole-1,3(2H)-dione (phthalimide) moiety. Quantitative study of substitution effect on the phthalimide moiety revealed that hydrophilic and electron-withdrawing groups enhance the activity.

Hydride Transfer Reaction Products in the Aminomethylation of Styrene

Aminomethylation of styrene with formaldehyde and dimethylamine leads to N-methylbenzenepropanamine (1), N-(3-phenylpropyl)benzenepropanamine (3), and α-methylenebenzenepropanal (4) as major products.The ratio of 1, 3 and 4 is considerably influenced by the ratio of the reactants.The best yield of 1 is obtained by using dimethylamine in excess.Styrene in excess favors the formation of 3, and equivalent amounts of reactants afford the best yield of 4.Using formaldehyde in excess leads to the complete N-methylation of 1 and 3.When styrene reacts with formaldehyde and diethylamine or diisopropylamine the most important aminomethylation products are N-ethylbenzenepropanamine (11) or N-isopropylbenzenepropanamine (12), respectively, and 3 and 4 in both cases.The formation of the major products in the aminomethylation of styrene can be explained by the hydride transfer mechanism represented earlier as one competing mechanism for the aminomethylation of certain bicyclic alkenes.The N-methylation of amine 1 and 3, when formaldehyde is used in excess, is due to Eschweiler methylation under aminomethylation conditions.