20390-68-5

Basic information

• Product Name: 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE
• Synonyms: 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE;1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZOAZEPINE;1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZOATE;1-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS NO: 20390-68-5
• Molecular Formula: C₁₆H₁₇N
• Molecular Weight: 223.31
• Mol File: 20390-68-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 365.4 °C at 760 mmHg
• Flash Point: 185.1 °C
• Appearance: /
• Density: 1.042 g/cm³
• Vapor Pressure: 1.58E-05mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE(20390-68-5)
• EPA Substance Registry System: 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE(20390-68-5)

Safety Data

• Hazardous Substances Data: 20390-68-5(Hazardous Substances Data)

Usage

General Description

1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE, also known as AH-5183, is a chemical compound with a benzazepine structure. It is a psychoactive drug that acts as a selective dopamine reuptake inhibitor. 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-BENZAZEPINE is often used in scientific research to study the effects of dopamine reuptake inhibition on behavior and neurotransmission. Additionally, it has shown potential as a treatment for conditions such as attention deficit hyperactivity disorder (ADHD) and other dopamine-related disorders. Its structure and mechanism of action make it a promising candidate for further development as a pharmaceutical compound.

InChI:InChI=1/C16H17N/c1-2-6-13(7-3-1)16-12-17-11-10-14-8-4-5-9-15(14)16/h1-9,16-17H,10-12H2

Upstream product

• 3469-06-5 benzocyclobutenone 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 139437-20-0 5-phenyl-1,3,4,5-tetrahydro-3(2H)-benzazepine-2-one 
• 112396-13-1 2-(2-bromophenyl)acetaldehyde dimethyl acetal 
• 5153-67-3 nitrostyrene 
• 112396-12-0 Homophthalaldehyd-monodimethylacetal 
• 691898-09-6 2-[2-(1-hydroxy-2-nitroethyl)phenyl]acetaldehyde dimethyl acetal 
• 198978-46-0 1-Phenyl-1,2-dihydro-benzo[d]azepine-3-carboxylic acid benzyl ester 
• 198978-43-7 2-[2-(2-nitro-1-phenylethyl)phenyl]acetaldehyde dimethyl acetal 

Downstream Products

• 129666-25-7 2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzoazepine 
• 228115-16-0 2-[4-(1-phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-butyl]-isoindol-1,3-dione 

Relevant articles and documents

A ring expansion strategy towards diverse azaheterocycles

The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C–C bond of strained ring ketones is first cleaved by the Pd0 species during the reaction. [Figure not available: see fulltext.].

Noncompetitive NMDA Antagonists: A novel synthesis of 1-phenyltetrahydro-3-benzazepines

The key step in the synthesis of the pharmacologically interesting l-phenyltetrahydro-3-benzazepine skeleton is the Michael addition of (2-lithiophenyl)acetaldehyde acetals, which are generated in situ upon treatment of the bromo acetals 5a,b with n-butyllithium, to β-nitrostyrene (6). The reductive ring closure of the nitro acetals 7a,b succeeded with zinc dust and hydrochloric acid to give the 3-benzazepines 11a,b in good yields. The unsubstituted 3-benzazepine 11a showed a considerable affinity for the phencyclidine binding site of the NMDA receptor (K(i) = 6.41 μM), whereas donor substituents in the aryl moiety (11b,c) reduce the affinity for the NMDA receptor.