rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one

Base Information

• Chemical Name: rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one
• CAS No.: 57452-32-1
• Molecular Formula: C₁₉H₂₂N₂O₃
• Molecular Weight: 326.395
• Mol file: 57452-32-1.mol

Synonyms:

Chemical Property of rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one

Chemical Property:

• Solubility.: Methanol

Purity/Quality:

98.5% ^*data from raw suppliers

rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one is an analogue of praziquantel (P702095), an anthelmintic that is effective against flatworms.

Technology Process of rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one

There total 16 articles about rac-1,2,3,6,7,11b-Hexahydro-2-[(4-oxocyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

4-oxocyclohexanecarboxylic acid (874-61-3) + (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one (55375-92-3,55375-90-1) → (-)-2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one (57452-32-1,94494-25-4,134924-66-6,134924-67-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/ardp.19913240409

Reference yield: 77.0%

4-oxocyclohexanecarboxylic acid (874-61-3) + (S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one (99746-73-3,55375-90-1) → (+)-2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one (57452-32-1,94494-25-4,134924-66-6,134924-67-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/ardp.19913240409

Reference yield: 50.0%

4-oxocyclohexanecarboxylic acid (874-61-3) + 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one (61196-37-0,55375-90-1) → 2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one (57452-32-1,134924-66-6,134924-67-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2010.03.001

upstream raw materials:

4-oxocyclohexane carboxylic acid chloride

2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one

4-oxocyclohexanecarboxylic acid

4-carbomethoxycyclohexanone

Downstream raw materials:

2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one

2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one

(+)-2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one

(+)-2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one

Refernces

• 1、 Dong, Yuxiang,Chollet, Jacques,Vargas, Mireille,Mansour, Nuha R.,Bickle, Quentin,Alnouti, Yazen,Huang, Jiangeng,Keiser, Jennifer,Vennerstrom, Jonathan L.. "Praziquantel analogs with activity against juvenile Schistosoma mansoni". scheme or table. p. 2481 - 2484. Retrieved 2010/07/16.