18655-50-0

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-CHLORO-PHENYL)-PROPYLAMINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Pesticide Industry:
In the pesticide sector, 3-(4-CHLORO-PHENYL)-PROPYLAMINE is utilized as an intermediate in the production of agrochemicals, contributing to the creation of effective pest control agents.
Used in Organic Chemical Synthesis:
3-(4-CHLORO-PHENYL)-PROPYLAMINE is employed as a versatile building block in the synthesis of a range of organic compounds, facilitating the development of novel chemical entities for diverse applications.

InChI:InChI=1/C9H12ClN/c10-9-5-3-8(4-6-9)2-1-7-11/h3-6H,1-2,7,11H2

Upstream product

• 184003-31-4 3-(4-Chloro-phenyl)-propionaldehyde O-methyl-oxime 
• 18166-64-8 4-chlorocinnamide 
• 5259-97-2 [1,3]oxazinan-2-one 
• 108-90-7 chlorobenzene 
• 2038-57-5 3-Phenylpropan-1-amine 
• 1615-02-7 p-chlorocinnamic acid 
• 35086-79-4 p-chlorocinnamoyl chloride 
• 75677-02-0 3-(4-chlorophenyl)propionaldehyde 
• 64473-35-4 3-(4-chlorophenyl)propyl bromide 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 1074-82-4 potassium phtalimide 
• 1336-21-6 ammonium hydroxide 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 

Downstream Products

• 26328-91-6 {5-[3-(4-chloro-phenyl)-propyl]-6-thioxo-[1,3,5]thiadiazinan-3-yl}-acetic acid 
• 26328-83-6 3-[3-(4-chloro-phenyl)-propyl]-5-(3-hydroxy-propyl)-[1,3,5]thiadiazinane-2-thione 
• 465528-61-4 2-{(1-(3-[4-chlorophenyl]propyl)aminocarbonyl)cyclopentylmethyl}-4-methoxybutyric acid tert-butyl ester 
• 374812-91-6 N-[3-(4-Chlorophenyl)propyl]-N-methyl-4-oxo-4-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butanamide 
• 374812-37-0 N-[3-(4-Chlorophenyl)propyl]-4-oxo-4-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butanamide 
• 1202890-30-9 ethyl 6-chloro-7-(4-(3-(4-chlorophenyl)propylcarbamoyl)phenoxy)chroman-4-carboxylate 
• 1660146-49-5 C₂₉H₂₇ClN₂O₃ 

Relevant academic research and scientific papers

Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides

The transition-metal-free intramolecular C-H amination of sulfamate esters using iodine oxidants, tert-butyl hypoiodite (t-BuOI) and N-iodosuccinimide (NIS) is reported. A method using NIS was also successfully applied to the oxidative cyclization of N-alkylsulfamides.

Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl] isothioureas: High affinity and human/rat species-selective histamine H 3 receptor antagonists

S-Alkyl-N-alkylisothiourea compounds containing various cyclic amines were synthesized in the search for novel nonimidazole histamine H3 receptor (H3R) antagonists. Among them, four N-alkyl S-[3-(piperidin-1-yl)propyl]isothioureas 18, 19, 22, and 23 were found to exhibit potent and selective H3R antagonistic activities against in vitro human H3R, but were inactive against in vitro human H 4R. Furthermore, three alkyl homologs 18-20 showed inactivity for histamine release in in vivo rat brain microdialysis, suggesting differences in antagonist affinities between species. In addition, in silico docking studies of N-[4-(4-chlorophenyl)butyl]-S-[3-piperidin-1-yl)propyl]isothiourea 19 and a shorter homolog 17 with human/rat H3Rs revealed that structural differences between the antagonist-docking cavities of rat and human H 3Rs were likely caused by the Ala122/Val122 mutation.

Aromatic chlorination of ω-phenylalkylamines and ω- phenylalkylamides in carbon tetrachloride and α,α,α- trifluorotoluene

The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω-phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α,α,α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement of N-chloroamines as reaction intermediates, with intramolecular delivery of the chlorine electrophile. ω-Phenylalkylamides, such as 3-phenylpropionamide, also easily undergo aromatic chlorination in carbon tetrachloride and α,α,α-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In α,α,α-trifluorotoluene, the rates reach a plateau at a chlorine concentration of approximately 0.2 M. These features indicate that the reactions proceed via the formation of intermediates which evidence suggests may be the corresponding O-chloroimidates. Irrespective of the mechanistic details, the reactions are remarkably rapid, being faster than analogous reactions in acetic acid and three to four orders of magnitude more rapid than reactions of simple alkylbenzenes in carbon tetrachloride. Therefore, chlorination of the amines and amides may be accomplished without the need for highly polar solvents, added catalysts or large excesses of chlorine, which are often employed for electrophilic aromatic substitutions. Although the use of carbon tetrachloride is becoming increasingly impractical due to environmental concerns, the trifluorotoluene is a suitable alternative. The Royal Society of Chemistry 2006.

Melanin-concentrating hormone antagonist

A melanin-concentrating hormone antagonist comprising a compound of the formula: wherein R is hydrogen atom or a cyclic group which may be substituted; X is a bond or a spacer having a main chain of 1 to 10 atoms; Y is a spacer having a main chain of 1 to 6 atoms; ring A is benzene ring which may be further substituted; ring B is a 5- to 9-membered nitrogen-containing non-aromatic heterocyclic ring which may be further substituted; R1 and R2 are the same or different and are hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; or R1 and R2, together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R2, together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or a salt thereof is useful as a preventive or therapeutic agent for obesity, etc.

N-phenpropylcuclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase

The invention relates to compounds of formula (I) for treating for example sexual dysfunction, wherein R1 is optionally substituted C1-6alkyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, hydrogen, C1-6alkoxy, —NR2 R3 or —NR4SO2R5; X is the linkage —(CH2)n— or —(CH2)q—O— (wherein Y is attached to the oxygen); wherein one or more hydrogen atoms in linkage X may be replaced independently by C1-4alkoxy; hydroxy; hydroxy(C1-3alkyl); C3-7cycloalkyl; carbocyclyl; heterocyclyl; or by C1-4alkyl optionally substituted by one or more fluoro or phenyl groups; n is 3, 4, 5, 6 or 7; and q is 2, 3, 4, 5 or 6; and Y is phenyl or pyridyl, each of which may be substituted; or two R8 groups on adjacent carbon atoms together with the interconnecting carbon atoms may form a fused optionally substituted 5- or 6-membered carbocyclic or heterocyclyic ring.

Imidazole compounds

A novel class of imidazo heterocyclic compounds, pharmaceutical compositions comprising them and use thereof in the treatment and/or prevention of diseases and disorders related to the histamine H3 receptor. More particularly, the compounds are useful for the treatment and/or prevention of diseases and disorders in which an interaction with the histamine H3 receptor is beneficial.

Synthesis, structure and quantitative structure-activity relationships of σ receptor ligands, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazines

A set of the title compounds having different substituents (R1, R2) on their phenyl groups was synthesized to find σ receptor binding affinity. Among the compounds, 2b (R1=R2=Cl) has the most potent σ1-binding activity, while 2a (R1=R2=H, SA4503) was most selective to σ1 over σ2 receptor. The crystal structures of 2a and 2b were shown, by X-ray crystallography, to be similar except for the one torsional angle of their propylene parts. Quantitative structure-activity relationship study suggested the affinity of the compounds to the σ1 receptor was dependent on the electronic feature, Swain-Lupton's R or S(π) that was derived by molecular orbital method, of R1 and R2.

Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 4. Potent, orally active analgesics

Structural features of three regions of the capsaicin molecule necessary for agonist properties were delineated by a previously reported modular approach. These in vitro agonist effects were shown to correlate with analgesic potency in rodent models. Comb

Novel phenylacetamide derivatives and processes for the preparation thereof

The present invention provides novel phenylacetamide derivatives having the following formula wherein:, X is a hydrogen, halogen, hydroxy, nitro, amino, R1, NR1R2, NHR1 or OR1 wherein R1 and R2 are an optionally substituted C1 8 alky

Phenylacetamide derivatives and pharmaceutical compositions thereof

The present invention provides novel phenylacetamide derivatives having the following formula STR1 wherein: X is a hydrogen, halogen, hydroxy, nitro, amino, R1, NR1 R2, NHR1 or OR1 wherein R1/su