9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol

Base Information

• Chemical Name: 9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol
• CAS No.: 104628-27-5
• Molecular Formula: C₂₁H₂₂N₂O₂
• Molecular Weight: 334.418
• DSSTox Substance ID: DTXSID50909074
• ChEMBL ID: CHEMBL53715
• Mol file: 104628-27-5.mol

Synonyms:9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol;1-Acridinol, 1,2,3,4-tetrahydro-9-(((3-methoxyphenyl)methyl)amino)-;104628-27-5;CHEMBL53715;BDBM9370;SCHEMBL9875331;DTXSID50909074;DKUJACOBAKIJQF-UHFFFAOYSA-N;9-Amino-1 ,2,3,4-tetrahydroacridin-1-ol deriv. 1x;9-(3-Methoxybenzylamino)-1,2,3,4-tetrahydroacridin-1-ol;9-(3-Methoxybenzylamino)-1,2,3,4-tetrahydroacridin-1ol;9-{[(3-methoxyphenyl)methyl]amino}-1,2,3,4-tetrahydroacridin-1-ol;9-{[(3-Methoxyphenyl)methyl]imino}-1,2,3,4,9,10-hexahydroacridin-1-ol

Chemical Property of 9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol

Chemical Property:

• Vapor Pressure: 9.86E-13mmHg at 25°C
• Boiling Point: 545.5°Cat760mmHg
• Flash Point: 283.7°C
• Density: 1.263g/cm³
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.168127949
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)CNC2=C3C(CCCC3=NC4=CC=CC=C42)O

Technology Process of 9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol

There total 6 articles about 9-(((3-Methoxyphenyl)methyl)amino)-1,2,3,4-tetrahydro-1-acridinol 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: 55.0%

3,4-dihydro-9-(3-methoxybenzylamino)acridin-1(2H)-one (104586-74-5) → 9-(3-Methoxybenzylamino)-1,2,3,4-tetrahydroacridin-1-ol (104628-27-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 2h;

DOI:10.1021/jm00128a024

Reference yield:

1,3-cylohexanedione (504-02-9) → 9-(3-Methoxybenzylamino)-1,2,3,4-tetrahydroacridin-1-ol (104628-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 91.9 percent / p-toluenesulfonic acid monohydrate / toluene / 2 h / Heating

2: 62.3 percent / K₂CO₃ / CuCl / tetrahydrofuran / 5 h / Heating

3: 72 percent / NaOH / 4N>4> / CH₂Cl₂; H₂O / 4 h

4: 55 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 2 h

With sodium hydroxide; lithium aluminium tetrahydride; potassium carbonate; toluene-4-sulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; copper(l) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jm00128a024

Reference yield:

9-Amino-1,2,3,4-tetrahydroacridin-1-one (104675-26-5) → 9-(3-Methoxybenzylamino)-1,2,3,4-tetrahydroacridin-1-ol (104628-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / NaOH / 4N>4> / CH₂Cl₂; H₂O / 4 h

2: 55 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 2 h

With sodium hydroxide; lithium aluminium tetrahydride; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1021/jm00128a024

upstream raw materials:

3,4-dihydro-9-(3-methoxybenzylamino)acridin-1(2H)-one

1,3-cylohexanedione

9-Amino-1,2,3,4-tetrahydroacridin-1-one

N-(3-oxocyclohexen-1-yl)-2-aminobenzonitrile

Refernces

• 1、 Shutske,Pierrat,Kapples,Cornfeldt,Szewczak,Huger,Bores,Haroutunian,Davis. "9-Amino-1,2,3,4-tetrahydroacridin-1-ols: Synthesis and evaluation as potential Alzheimer's disease therapeutics". . p. 1805 - 1813. Retrieved 2007/10/02.
• 2、 -. "9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds". . . Retrieved 2008/06/13.