1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole

Base Information

• Chemical Name: 1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole
• CAS No.: 103610-04-4
• Molecular Formula: C₂₅H₂₄N₂O₂
• Molecular Weight: 384.478
• UNII: 9HN5J913P3
• DSSTox Substance ID: DTXSID60145946
• Nikkaji Number: J378.966G
• Wikipedia: JWH-200
• Wikidata: Q4041745
• Pharos Ligand ID: 1BNXAULTMA7F
• ChEMBL ID: CHEMBL13078
• Mol file: 103610-04-4.mol

Synonyms:103610-04-4;JWH-200;1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole;[1-[2-(4-Morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenylmethanone;JWH 200;UNII-9HN5J913P3;DEA No. 7200;HSDB 8000;9HN5J913P3;(1-(2-morpholinoethyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone;CHEMBL13078;1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl)indole;SCHEMBL10093017;DTXSID60145946;SZWYXJHTNGJPKU-UHFFFAOYSA-N;BDBM50009854;WIN-55255;AKOS015909676;CCG-208717;J378.966G;JWH-200 (WIN 55,225);FT-0672531;FT-0672532;Q-200038;Q4041745;(1-(2-Morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-yl)methanone;[1-(2-morpholin-4-ylethyl)indol-3-yl]-naphthalen-1-ylmethanone;1-(2-(4-MORPHOLINYL)ETHYL)-3-(1-NAPHTHOYL)INDOLE [HSDB];1-naphthalenyl(1-(2-(4-morpholinyl)ethyl)-1h-indol-3-yl)methanone;[1-(2-Morpholin-4-yl-ethyl)-1H-indol-3-yl]-naphthalen-1-yl-methanone;METHANONE, (1-(2-(4-MORPHOLINYL)ETHYL)-1H-INDOL-3-YL)-1-NAPHTHALENYL-

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Chemical Property of 1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 104-106 ºC
• Boiling Point: 601.997°C at 760 mmHg
• PKA: 7.04±0.10(Predicted)
• Flash Point: 317.877°C
• PSA: 34.47000
• Density: 1.21
• LogP: 4.29560
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 384.183778013
• Heavy Atom Count: 29
• Complexity: 561

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1CCN2C=C(C3=CC=CC=C32)C(=O)C4=CC=CC5=CC=CC=C54
• Uses: An analgesic compound which acts as a partial agonist at both the CB1 and CB2 cannabinoid receptors.

Technology Process of 1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole

There total 3 articles about 1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole 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: 63.0%

carbon monoxide (201230-82-2) + 1-Naphthylboronic acid (13922-41-3) + C14H17IN2O → [1-[2-(morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenyl-methanone (103610-04-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; triethylamine; In 1,4-dioxane; at 80 ℃; for 20h; Inert atmosphere; Sealed tube; Cooling with ice;

DOI:10.1039/c9ra06594f

Reference yield: 62.0%

1-<2-(4-morpholinyl)ethyl>-1H-indole (72395-48-3) + naphthalene-1-carbonic acid chloride (879-18-5) → [1-[2-(morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenyl-methanone (103610-04-4)

Guidance literature:

With aluminium trichloride; In 1,2-dichloro-ethane;

DOI:10.1021/jm00107a034

Reference yield:

3-Iodo-1H-indole (26340-47-6) → [1-[2-(morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenyl-methanone (103610-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 4 h / 20 °C

2: triethylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate / 1,4-dioxane / 20 h / 80 °C / Inert atmosphere; Sealed tube; Cooling with ice

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium hydride; potassium carbonate; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1039/c9ra06594f

upstream raw materials:

1-<2-(4-morpholinyl)ethyl>-1H-indole

naphthalene-1-carbonic acid chloride

3-Iodo-1H-indole

carbon monoxide