ChemicalBook > CAS DataBase List > Azepindole

Azepindole

Product Name
Azepindole
CAS No.
26304-61-0
Chemical Name
Azepindole
Synonyms
McN-2453;Azepindole;2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,2-a]indole;1H-[1,4]Diazepino[1,2-a]indole, 2,3,4,5-tetrahydro-
CBNumber
CB11178073
Molecular Formula
C12H14N2
Formula Weight
186.25
MOL File
26304-61-0.mol
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Azepindole Property

Boiling point:
367.1±17.0 °C(Predicted)
Density 
1.19±0.1 g/cm3(Predicted)
pka
10.85±0.20(Predicted)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Biosynth Carbosynth
Product number
FA168210
Product name
Azepindole
Packaging
25mg
Price
$300
Updated
2021/12/16
Biosynth Carbosynth
Product number
FA168210
Product name
Azepindole
Packaging
50mg
Price
$400
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM1039886
Product name
1H,2H,3H,4H,5H-[1,4]DIAZEPINO[1,2-A]INDOLE
Purity
95.00%
Packaging
5MG
Price
$497.32
Updated
2021/12/16
Biosynth Carbosynth
Product number
FA168210
Product name
Azepindole
Packaging
100mg
Price
$500
Updated
2021/12/16
AK Scientific
Product number
2623CA
Product name
Azepindole
Packaging
50mg
Price
$590
Updated
2021/12/16
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Azepindole Chemical Properties,Usage,Production

Originator

Azependole,ZYF Pharm Chemical

Uses

Antidepressant.

Manufacturing Process

Ethyl indole-2-carboxylate (9.84 g, 0.052 mole) is dissolved in 150 ml dioxane. Acrylonitrile (3.11 g, 0.0588 mole) and benzyltrimethylammonium hydroxide (Triton B) (2 ml) are added and the mixture is warmed, with stirring, at 50°-55°C for 45 min. The solution is cooled to room temperature and stirred overnight. The reaction mixture is added to 500 ml water containing 3 ml glacial acetic acid. The mixture is extracted with methylene chloride, the organic layer washed with 2x25 ml water and dried over magnesium sulfate. The solvent is removed under reduced pressure. The remaining oil is dissolved in ether and filtered through alumina with ether as eluant. Evaporation of the ether gives a solid. The product obtained is ethyl N- (β-cyanoethyl)indole-2-carboxylate, melting point 84°-86°C.
A 2.42 g (0.01 mole) of ethyl N-(β-cyanoethyl)indole-2-carboxylate is suspended in acetic anhydride (20 ml). The suspended compound is hydrogenated on a Parr shaker in the presence of Raney nickel. The uptake of hydrogen is complete after 1.5 h. The product recovered is recrystallized from benzene-hexane. The product obtained is ethyl 1-(3-acetamidopropyl)indole- 2-carboxylate, melting point 83.5°-84.5°C.
Ethyl 1-(3-acetamidopropyl)indole-2-carboxylate (1.44 g, 0.005 mole) is cyclized in the presence of sodium hydride (0.30 g, 0.00625 molar in hydride) in xylene under reflux. A few drops of absolute ethanol are added after 1 h reflux. Total reflux time is 2 h. The product recovered is crystallized from benzenehexane. The product obtained is 2,3,4,5-tetrahydro-1H-1,4- diazepino[1,2-a]indol-1-one, melting point 181°-183°C.
2,3,4,5-Tetrahydro-1H-1,4-diazepino[1,2-a]indol-1-one (6.0 g, 0.03 mole) in 200 ml of monoglyme is added dropwise to a stirred suspension of lithium aluminum hydride (2.8 g, 0.08 mole) in 200 ml of monoglyme, and the mixture heated under reflux overnight. Water is added to the cooled mixture, and the mixture filtered. The filtrate is dried with anhydrous magnesium sulfate and concentrated in vacuum, giving an oil which solidifies on standing to give about 85% theoretical yield of the free amine, 2,3,4,5-tetrahydro-1H- 1,4-diazepino[1,2a]indol, melting point 75°-77°C.

Therapeutic Function

Antidepressant

Azepindole Preparation Products And Raw materials

Raw materials

Preparation Products

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Azepindole Suppliers

Lanospharma Laboratories Co.,Ltd
Tel
--
Fax
--
Email
sales@lanospharma.com
Country
China
ProdList
6329
Advantage
56
Shanghai New Union Textra Import & Export Co., Ltd
Tel
--
Fax
--
Email
zhou@pharmchemical.com
Country
China
ProdList
2748
Advantage
60