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

Ipidacrine is used in biological studies as a possible treatment of toxic cognitive 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

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