l-Praziquantel

Base Information

• Chemical Name: l-Praziquantel
• CAS No.: 57452-98-9
• Molecular Formula: C19H24N2O2
• Molecular Weight: 312.41
• Mol file: 57452-98-9.mol

Synonyms:(R)-(-)-Praziquantel;4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (11bR)- (9CI);4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (R)-;l-Praziquantel

Chemical Property of l-Praziquantel

Chemical Property:

• Melting Point: 113-115 °C
• Boiling Point: 544.1±50.0 °C(Predicted)
• PKA: -0.98±0.20(Predicted)
• PSA: 40.62000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 2.41070
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

(R)-Praziquantel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-Praziquantel is the active enantiomer of praziquantel regarding activity against juvenile S. mansoni infestations in mice. (R)-Praziquantel exhibits Schistosoma mansoni infestation inhibition in vitro and in vivo.

Technology Process of l-Praziquantel

There total 180 articles about l-Praziquantel 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: 95.0%

4-(cyclohexylcarbonyl)-6-hydroxy-1-phenethylpiperazine-2-one (87693-75-2) → 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one (55268-74-1,135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

With hydrogenchloride; at 0 ℃;

Reference yield: 95.0%

4-(cyclohexylcarbonyl)-6-hydroxy-1-phenethylpiperazine-2-one (87693-75-2) → 2-(cyclohexylcarbonyl)-1,3,4,6,7,11b-hexahydro-2H-pyrazino-(2,1-a)-4-isoquinoleinone (PRAZIQUANTEL) + 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one (55268-74-1,135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

In 12N-hydrochloric acid;

Reference yield: 93.0%

2-(Cyclohexylcarbonyl)-2,3,6,7-tetrahydro-4H-pyrazino-<2,1-a>-isoquinolin-4-one (125273-86-1) → 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one (55268-74-1,135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 19h; under 760.051 Torr; Solvent; Inert atmosphere;

DOI:10.1016/j.tet.2017.10.006

upstream raw materials:

N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide

chloroacetyl chloride

1-Cyclohexylcarbonylaminomethyl-2-chloracetyl-1,2,3,4-tetrahydro-isochinolin

Cyclohexanecarboxylic acid bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl-[(methoxymethyl-carbamoyl)-methyl]-amide

Downstream raw materials:

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

C₂₃H₂₃N₃O₂

C₃₄H₄₀N₆O₄

Refernces

• 1、 Pedersen, Simon S.,Donslund, Aske S.,Mikkelsen, Jesper H.,Bakholm, Oskar S.,Papp, Florian,Jensen, Kim B.,Gustafsson, Magnus B. F.,Skrydstrup, Troels. "A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides". supporting information. p. 7114 - 7123. Retrieved 2021/03/03.
• 2、 He, Zhaoting,Peng, Gang,Shou, Haowen,Su, Weike,Yu, Jingbo. "Two approaches for the synthesis of levo-praziquantel". . p. 4507 - 4514. Retrieved 2021/05/31.