54761-87-4

Basic information

• Product Name: 2-BENZYL-1,2,3,6,7,11B-HEXAHYDRO-4H-PYRAZION[2,1-A] ISOQUINOLINE-4-ONE
• Synonyms: 2-BENZYL-1,2,3,6,7,11B-HEXAHYDRO-4H-PYRAZION[2,1-A] ISOQUINOLINE-4-ONE;2-Benzoyl-1,2,3,6,7,11b-Hexahydro-4H-pyrazino[2,1-a]isoquinoline-4-one;2-BENZOYL-1,2,3,6,7,11B-HEXAHYDRO-PYRAZINO[2,1-A]ISOQUINOLIN-4-ONE ;2-Benzoyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-;Praziquantel Intermediates;2-benzoyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino [2,1-a]isoquinolin-4-one;Praziquantel Related CoMpound A;Praziquantel Related Compound A (20 mg) (2-benzoyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino [2,1-a]isoquinolin-4-one)
• CAS NO: 54761-87-4
• Molecular Formula: C₁₉H₁₈N₂O₂
• Molecular Weight: 292.37
• Mol File: 54761-87-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 539.904 °C at 760 mmHg
• Flash Point: 256.971 °C
• Appearance: /
• Density: 1.308 g/cm³
• Vapor Pressure: 1.01E-11mmHg at 25°C
• Refractive Index: 1.672
• PKA: -1.16±0.20(Predicted)
• CAS DataBase Reference: 2-BENZYL-1,2,3,6,7,11B-HEXAHYDRO-4H-PYRAZION[2,1-A] ISOQUINOLINE-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYL-1,2,3,6,7,11B-HEXAHYDRO-4H-PYRAZION[2,1-A] ISOQUINOLINE-4-ONE(54761-87-4)
• EPA Substance Registry System: 2-BENZYL-1,2,3,6,7,11B-HEXAHYDRO-4H-PYRAZION[2,1-A] ISOQUINOLINE-4-ONE(54761-87-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 54761-87-4(Hazardous Substances Data)

Usage

Uses

2-(Descyclohexylcarbonyl)-2-benzoyl Praziquantel is used in the synthesis of Praziquantel (P702095), anthelmintic, effective against flatworms. Praziquantel USP Related Compound A

InChI:InChI=1/C19H18N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h1-9,17H,10-13H2

Upstream product

• 100-52-7 benzaldehyde 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 98-88-4 benzoyl chloride 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 59795-89-0 phenethyl isocyanide 
• 65-85-0 benzoic acid 
• 90142-12-4 C₂₁H₂₆N₂O₄ 
• 87693-78-5 4-benzoyl-2,6-dioxo-1-phenethyl piperazine 
• 87693-76-3 4-benzoylpiperazine-2,6-dione 
• 17376-04-4 2-phenethyl iodide 
• 152189-69-0 N-cyanomethylhippuric acid 
• 3591-82-0 2-phenylethylaminoacetonitrile 
• 495-69-2 Hippuric Acid 
• 152189-68-9 N-(2-phenylethyl)-N-(cyanomethyl)amide of hippuric acid 

Downstream Products

• 105279-85-4 2-benzyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 

Relevant articles and documents

Combining Incompatible Processes for Deracemization of a Praziquantel Derivative under Flow Conditions

An efficient deracemization method for conversion of the racemate to the desirable (R)-enantiomer of Praziquantel has been developed by coupling incompatible racemization and crystallization processes. By a library approach, a derivative that crystallizes as a conglomerate has been identified. Racemization occurs via reversible hydrogenation over a palladium on carbon (Pd/C) packed column at 130 °C, whereas deracemization is achieved by alternating crystal growth/dissolution steps with temperature cycling between 5–15 °C. These incompatible processes are combined by means of a flow system resulting in complete deracemization of the solid phase to the desired (R)-enantiomer (98 % ee). Such an unprecedented deracemization by a decoupled crystallization/racemization approach can readily be turned into a practical process and opens new opportunities for the development of essential enantiomerically pure building blocks that require harsh methods for racemization.

MCR Synthesis of Praziquantel Derivatives

Schistosomiasis, a high volume neglected tropical disease affecting more than 200 million people worldwide, can only be effectively treated by the tetrahydroisoquinoline drug praziquantel (PZQ). Herein, we describe an efficient approach to access PZQ derivatives by the Ugi 4-component reaction followed by the Pictet-Spengler reaction in a two-step, one-pot procedure. 30 novel PZQ derivatives are described based on the Ugi 4-component reaction and an X-ray structure of a novel derivative revealing different conformation compared with PZQ is discussed. Several analogues comparable in activity to the drug PZQ have been identified based on an in vitro Schistosoma mansoni worm viability assay.

USE OF INTERPHASE CATALYSIS IN THE SYNTHESIS OF 2-ACYL-4-OXOPYRAZINOISOQUINOLINES AND 4-ACYL-2-PIPERAZINONES

2-acetyl-4-oxopyrazinoisoquinolines and 4-acyl-2-piperazinones have been synthesized, with interphase catalysis, by the intramolecular N-alkylation of the corresponding diamides.