62732-44-9

Basic information

• Product Name: 2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE
• Synonyms: 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta(b)quinoline monohydrochloride;MFCD11052605;1H,2H,3H,5H,6H,7H,8H-Cyclopenta[b]quinolin-9-amine;CBI-BB ZERO/005050;AURORA KA-7699;2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE;9-AMINO-2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLINE;AKOS MSC-0106
• CAS NO: 62732-44-9
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27
• EINECS: 676-166-9
• Mol File: 62732-44-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 202-203 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 367.969 °C at 760 mmHg
• Flash Point: 203.991 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• PKA: 10.88±0.20(Predicted)
• CAS DataBase Reference: 2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE(62732-44-9)
• EPA Substance Registry System: 2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE(62732-44-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 62732-44-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE is used as a potential therapeutic agent for the treatment of toxic cognitive disorders. Its unique molecular structure allows it to interact with specific biological targets, potentially modulating the underlying mechanisms of these disorders and providing relief to affected individuals.
Used in Biological Studies:
In the field of biological research, 2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE serves as a valuable tool for studying the molecular mechanisms underlying various cognitive and neurological conditions. Its interactions with biological systems can provide insights into the development of novel therapeutic strategies and help researchers better understand the complex processes involved in these disorders.

InChI:InChI=1/C12H16N2/c13-12-8-4-1-2-6-10(8)14-11-7-3-5-9(11)12/h1-7H2,(H2,13,14)

Synthetic route

diphosphorus pentaoxide (P2O0) + triethyl phosphate (78-40-0) + 2-amino-1-cyanocyclopentene (2941-23-3) → NIK247 (62732-44-9)

Conditions	Yield
With sodium hydroxide In methanol; ethanol; water; cyclohexanone; toluene	91%

4'-Oxo-spiropyrimidin> (58996-10-4) → NIK247 (62732-44-9)

Conditions	Yield
With trichlorophosphate In toluene for 24h; Heating;	79%
With trichlorophosphate In toluene for 24h; Mechanism; Heating; other time; various ratio POCl3/educt;	79%

cyclohexanone (108-94-1) + 2-amino-1-cyanocyclopentene (2941-23-3) → NIK247 (62732-44-9)

Conditions	Yield
With zinc(II) chloride In xylene Heating;

NIK247 (62732-44-9) + methyl iodide (74-88-4) → 4-methyl-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopentaquinoline iodide

Conditions	Yield
In methanol at 40℃;	92%

NIK247 (62732-44-9) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions	Yield
In chloroform at 0℃; for 1h; Reflux;	2 g

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-(4-(pyridin-2-yl)piperazin-1-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → 2-(4-benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-{4-[(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-ylcarbamoyl)methyl]piperazin-1-yl}acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1150 °C View Scheme

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-(4-methylpiperazin-1-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → 4-[(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-ylcarbamoyl)methyl]piperazine-1-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-(4-cyclohexylpiperazin-1-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → 2-(4-benzhydrylpiperazin-1-yl)-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-[4-(2-methoxyphenyl)piperazin-1-yl]acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

NIK247 (62732-44-9) → 2-[4-(4-acetylphenyl)piperazin-1-yl]-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 1 h / 0 °C / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

Upstream product

• 58996-10-4 4'-Oxo-spiropyrimidin> 
• 78-40-0 triethyl phosphate 
• 2941-23-3 2-amino-1-cyanocyclopentene 
• 108-94-1 cyclohexanone 

Relevant articles and documents

Process for the preparation of ipidacrine or ipidacrine hydrochloride hydrate

A process for the preparation of ipidacrine (I) (9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline) which comprises the reaction of diphosphorus pentaoxide with a trialkyl phosphate and a hydroxyl compound in a hydrocarbon solvent to thereby prepare a polyphosphoric ester having one or more free hydroxyl groups and serving as a dehydrocondensing agent and using this ester without isolation in the condensation of 2-amino-1-cyclopentene-1-carbonitrile with cyclohexanone through dehydration.

Recyclization of 2,2-Disubstituted 4(3H)-Oxo- and 4-Chloro-1,2-dihydropyrimidines to 4-Aminopyridine Derivatives

The intramolecular cationotropic rearrangement of salts of two-ring 2,2-disubstituted 4-chloro-1,2-dihydropyrimidines to 4-aminopyrimidine derivatives was observed.Recyclization to 4-aminopyridines can take place in the reaction of two-ring 2,2-disubstituted 4(3H)-oxo-1,2-dihydropyrimidines with phosphorus oxychloride without isolation of the intermediate chloro derivatives.A probable mechanism that makes it possible to assert that the observed recyclization is a variant of the intramolecular cationotropic rearrangement that is characteristic for 2,2-dialkylsubstituted 1,2-dihydropyrimidines with functional substituents (for example, oxo or chloro) in the 4 position of the ring is discussed.