N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide

Base Information

• Chemical Name: N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide
• CAS No.: 196597-17-8
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• DSSTox Substance ID: DTXSID80432305
• ChEMBL ID: CHEMBL134330
• Mol file: 196597-17-8.mol

Synonyms:196597-17-8;N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide;N-[2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethyl]propanamide;Propanamide,N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]-;NCGC00095187-01;N-(2-{1H,2H,6H,7H,8H-INDENO[5,4-B]FURAN-8-YL}ETHYL)PROPANAMIDE;N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide;DTXSID6045951;Remelteon;rac ramelteon;(Rac)-Remelteon;SCHEMBL338730;CHEMBL134330;DTXCID4025951;DTXSID80432305;HMS3657C11;HMS3745O03;BCP04205;BCP18306;CS-M2669;WHA59717;DISCONTINUED. See R110051;Tox21_111476;DISCONTINUED. See R110051";AKOS037650069;PB27872;NCGC00095187-02;CS-14200;TAK-375;Rozerem;TAK375;TAK 375;CAS-196597-26-9;FT-0655799;FT-0674313;EN300-1694967;A813859;A899505;L001280

Chemical Property of N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide

Chemical Property:

• Boiling Point: 467.111 °C at 760 mmHg
• Flash Point: 236.3 °C
• PSA: 41.82000
• Density: 1.119 g/cm³
• LogP: 3.40790
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 331

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)NCCC1CCC2=C1C3=C(C=C2)OCC3
• Uses: Melatonin MT1/MT2 receptor agonist. Sedative, hypnotic.

Technology Process of N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide

There total 110 articles about N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide 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: 97.4%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride + propionyl chloride (79-03-8) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;

Reference yield: 90.0%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine (196597-81-6) + propionyl chloride (79-03-8) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 86.0%

methanesulfonyl chloride (124-63-0) + (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-88-3) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

methanesulfonyl chloride; (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide; With pyridine; at -10 - -5 ℃; for 0.833333h;

With triethylamine; In ethyl acetate; Further stages.; Heating;

DOI:10.1021/jm0201159

upstream raw materials:

methanesulfonyl chloride

(S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide

propionyl chloride

2-(1,6-dihydro-2H-indeno[5,4-b]furan-8-yl)acetamide

Refernces

• 1、 Gao, Shijun,Qian, Guangyin,Tang, Hao,Yang, Zuo,Zhou, Qianghui. "Three-Step Total Synthesis of Ramelteon via a Catellani Strategy". . p. 5762 - 5765. Retrieved 2019.
• 2、 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.