2-(2-Morpholinoethyl)isoindoline-1,3-dione

Base Information

• Chemical Name: 2-(2-Morpholinoethyl)isoindoline-1,3-dione
• CAS No.: 6820-90-2
• Molecular Formula: C14H16N2O3
• Molecular Weight: 260.293
• DSSTox Substance ID: DTXSID10354703
• Wikidata: Q82133038
• ChEMBL ID: CHEMBL1893667
• Mol file: 6820-90-2.mol

Synonyms:2-(2-morpholinoethyl)isoindoline-1,3-dione;6820-90-2;2-(2-morpholin-4-ylethyl)isoindole-1,3-dione;2-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione;ST012869;ChemDiv2_006496;Oprea1_479929;Oprea1_630358;MLS000116906;2-(2-morpholin-4-ylethyl)benzo[c]azoline-1,3-dione;SCHEMBL8556230;CHEMBL1893667;DTXSID10354703;HMS1387H08;HMS2264C12;HMS3440D09;AKOS000577065;AM87137;IDI1_005211;SMR000093860;CS-0349202;Z54747695

Chemical Property of 2-(2-Morpholinoethyl)isoindoline-1,3-dione

Chemical Property:

• PSA: 49.85000
• LogP: 0.49060
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 260.11609238
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

95% ^*data from raw suppliers

N-(2-Morpholinoethyl)-phthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1CCN2C(=O)C3=CC=CC=C3C2=O
• Uses: N-(2-Morpholinoethyl)-phthalimide is an intermediate in the synthesis of Moclobemide-d8 which is the labeled analogue of Moclobemide (M481000), a reversible monoamine oxidase inhibitor.

Technology Process of 2-(2-Morpholinoethyl)isoindoline-1,3-dione

There total 5 articles about 2-(2-Morpholinoethyl)isoindoline-1,3-dione 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%

morpholine (110-91-8,99108-56-2) + 2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) → 2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione (6820-90-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100 ℃; for 18h;

DOI:10.1021/acs.jmedchem.9b01012

Reference yield: 62.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + trimethylsilyl cyanide (7677-24-9) + 2-Iodobenzoic acid (88-67-5) → 2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione (6820-90-2)

Guidance literature:

With copper(I) oxide; water; at 100 ℃; for 8h; Green chemistry;

DOI:10.1039/d1ob00073j

Reference yield:

potassium phtalimide (1074-82-4) → 2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione (6820-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 20 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 100 °C

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.9b01012

upstream raw materials:

N-(2-chlorethyl)morpholine

potassium phtalimide

morpholine

2-(2-bromoethyl)isoindoline-1,3-dione

Downstream raw materials:

4-nitrophenyl (2-morpholinoethyl)carbamate

4-(2-AMINOETHYL)MORPHOLINE

Refernces

• 1、 -. "COMPOUND INHIBITING BUTYRYLCHOLINESTERASE". Page/Page column 9. . Retrieved 2020/07/31.
• 2、 Tazarki, Helmi,Zeinyeh, Wael,Esvan, Yannick J.,Knapp, Stefan,Chatterjee, Deep,Schr?der, Martin,Joerger, Andreas C.,Khiari, Jameleddine,Josselin, Béatrice,Baratte, Blandine,Bach, Stéphane,Ruchaud, Sandrine,Anizon, Fabrice,Giraud, Francis,Moreau, Pascale. "New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis". . p. 304 - 317. Retrieved 2019/02/07.