2156-27-6

Basic information

• Product Name: BENPROPERINE
• Synonyms: BENPROPERINE;1-(1-methyl-2-((alpha-phenyl-o-tolyl)oxy)ethyl)-piperidin;1-(1-methyl-2-((alpha-phenyl-o-tolyl)oxy)ethyl)piperidine;1-(1-methyl-2-(2-(phenylmethyl)phenoxy)ethyl)-piperidin;1-(2-(2-benzilfenossi)-1-metiletil)-piperidina;pirexyl;Benproperin;1-[2-(2-Benzylphenoxy)-1-methylethyl]piperidine
• CAS NO: 2156-27-6
• Molecular Formula: C₂₁H₂₇NO
• Molecular Weight: 309.45
• EINECS: 1308068-626-2
• Mol File: 2156-27-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: bp0.2 159-161°
• Flash Point: 126.8 °C
• Appearance: /
• Density: 1.0350 (rough estimate)
• Refractive Index: 1.5614 (estimate)
• PKA: 9.46±0.50(Predicted)
• CAS DataBase Reference: BENPROPERINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENPROPERINE(2156-27-6)
• EPA Substance Registry System: BENPROPERINE(2156-27-6)

Safety Data

• Hazardous Substances Data: 2156-27-6(Hazardous Substances Data)

Usage

Originator

Tussafug,Medipharm,Switz.

Manufacturing Process

A mixture of 26.1 g of o-benzylphenoxy-β-chloropropane and 17 g of piperidine is refluxed over a period of 32 hours until the temperature is about 124°C and a nearly solid mixture is formed due to the precipitation of a salt. The mixture is then refluxed over a period of 48 hours at about 160°C and the reaction product obtained is cooled and dissolved in methanol. The solution is concentrated under reduced pressure to yield an oil which is added to 200 ml 3N hydrochloric acid whereupon the mixture is shaken with ether, 3 x 100 ml, until the aqueous phase is clear. The ether solution is washed with water, 3 x 50 ml, and the water present in the combined aqueous phase and water used for washing is evaporated under reduced pressure methanol being added three times when the residue appears to be dry. The impure hydrochloride of o-benzylphenoxy-β-N-piperidinopropane, 41 g, obtained is dissolved in 100 ml water and 100 ml 30% aqueous sodium hydroxide solution are added, whereupon precipitated oil is extracted with ether, 1 x 100 and 2 x 50 ml. The ether solution is washed with water, 4 x 50 ml, dried with magnesium sulfate and the ether is removed under reduced pressure. The residue, 25.2 g, is distilled under reduced pressure and the main fraction, 23.2 g, BP 159°-161°C/0.2 mm.

Therapeutic Function

Antitussive

InChI:InChI=1/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3

Upstream product

• 98569-93-8 1-(allyloxy)-2-benzylbenzene 
• 5029-76-5 (2-benzylphenoxy)-2-propanol 
• 100-51-6 benzyl alcohol 
• 108-95-2 phenol 
• 110-89-4 piperidine 
• 85909-36-0 (2-benzyl-phenyl)-(2-chloro-propyl)-ether 
• 28994-41-4 o-Benzylphenol 

Downstream Products

• 124678-31-5 Benproperine phosphate 

Relevant articles and documents

Photoinduced Olefin Diamination with Alkylamines

Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.

COMPOSITION COMPRISING BENPROPERINE DERIVATIVES AS ACTIVE INGREDIENTS FOR PREVENTING AND TREATING ANGIOGENESIS-RELATED DISEASES

The present invention relates to a novel pharmaceutical composition of benproperine derivatives for preventing and treating angiogenesis-related diseases. The benproperine derivatives and pharmaceutically acceptable salts thereof according to the present invention inhibit cancer cell migration and the angiogenesis of vascular endothelial cells, and therefore can be effectively used not only as an anticancer agent, but also as an agent for preventing and treating diseases caused by abnormal angiogenesis, such as diabetic retinopathy and corneal transplant rejection.