cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide

Base Information

• Chemical Name: cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide
• CAS No.: 105310-75-6
• Molecular Formula: C23H24N2O3
• Molecular Weight: 376.455
• Hs Code.: 2925190100
• European Community (EC) Number: 692-500-6
• DSSTox Substance ID: DTXSID201110472
• Nikkaji Number: J2.288.818H
• Wikidata: Q76423320
• Mol file: 105310-75-6.mol

Synonyms:105310-75-6;cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide;(1R,2S)-2-[(1,3-DIOXOISOINDOL-2-YL)METHYL]-N,N-DIETHYL-1-PHENYLCYCLOPROPANE-1-CARBOXAMIDE;cis-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxamide;(1R,2S)-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxami;(1R,2S)-2-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenyl-1-cyclopropane carboxamide;SCHEMBL9993898;DTXSID201110472;rel-(1R,2S)-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxamide;AKOS015896478;DS-8344;(1R,2S)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide;CS-0152041;C71215;(1R,2S)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide;cis-2-(1,3-dihydro-1,3-dioxo-2h-isoindol-2-yl)methyl-n,n-diethyl-1-phenylcyclopropanecarboxamide

Chemical Property of cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide

Chemical Property:

• Vapor Pressure: 1.52E-11mmHg at 25°C
• Melting Point: 130-132 °C
• Refractive Index: 1.638
• Boiling Point: 546.101 °C at 760 mmHg
• PKA: -0.68±0.40(Predicted)
• Flash Point: 237.521 °C
• PSA: 57.69000
• Density: 1.254 g/cm³
• LogP: 3.04680
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 376.17869263
• Heavy Atom Count: 28
• Complexity: 614

Purity/Quality:

98%, ^*data from raw suppliers

rel-(1R,2S)-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1(CC1CN2C(=O)C3=CC=CC=C3C2=O)C4=CC=CC=C4
• Isomeric SMILES: CCN(CC)C(=O)[C@@]1(C[C@@H]1CN2C(=O)C3=CC=CC=C3C2=O)C4=CC=CC=C4
• Uses: Milnacipran intermediate Milnacipran intermediate.

Technology Process of cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide

There total 17 articles about cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide 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: 85.1%

C20H17NO4 + diethylamine (109-89-7) → (1SR,2RS)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane carboxamide (105310-75-6)

Guidance literature:

With sodium amide; In toluene; Reagent/catalyst;

Reference yield:

C19H14ClNO3 + diethylamine (109-89-7) → (1SR,2RS)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane carboxamide (105310-75-6)

Guidance literature:

In dichloromethane; at 0 - 30 ℃; for 4.75h;

Reference yield:

(1SR,2RS)-2-(chloromethyl)-N,N-diethyl-1-phenylcyclopropane carboxamide (1353644-50-4) + potassium phtalimide (1074-82-4) → (1SR,2RS)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane carboxamide (105310-75-6)

Guidance literature:

In dichloromethane; at 0 - 45 ℃; Product distribution / selectivity;

upstream raw materials:

potassium phtalimide

(Z)-1-phenyl-2-(bromomethyl)-N,N-diethylcyclopropanecarboxamide

(1S,2R)/(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid

(1S,2R)/(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid chloride

Downstream raw materials:

cis-(±)-1-phenyl-2-(aminomethyl)-N,N-diethylcyclopropanecarboxamide hydrochloride

(1R,2S)-2-{[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-methyl}-1-phenyl-cyclopropanecarboxylic acid diethylamide

(Z)-1-phenyl-2-<(glycylamino)methyl>-N,N-diethylcyclopropanecarboxamide

Z-1-phenyl-2-<(acetylamino)methyl>-N,N-diethylcyclopropanecarboxamide

Refernces

• 1、 Raja Gopal,Christy Prabakar,Chandrashekar,Vijaya Bhaskard,Veera Somaiah. "Synthesis and characterization of process related impurities of (±)-Milnacipran". . p. 639 - 644. Retrieved 2013/10/22.
• 2、 -. "PROCESS FOR PREPARATION OF MILNACIPRAN INTERMEDIATE AND ITS USE IN PREPARATION OF PURE MILNACIPRAN". Page/Page column 24-25. . Retrieved 2012/01/06.