3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone

Base Information

• Chemical Name: 3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone
• CAS No.: 104675-27-6
• Molecular Formula: C20H18N2O
• Molecular Weight: 302.376
• DSSTox Substance ID: DTXSID40399723
• Wikidata: Q82202426
• Mol file: 104675-27-6.mol

Synonyms:104675-27-6;3,4-DIHYDRO-9-[(BENZYL)AMINO]-1(2H)-ACRIDINONE;9-(benzylamino)-3,4-dihydro-2H-acridin-1-one;9-(benzylamino)-3,4-dihydroacridin-1(2H)-one;SCHEMBL8984077;DTXSID40399723;JMKIIRWHVISOBM-UHFFFAOYSA-N;STK283507;9-benzylamino-3,4dihydroacridin-1(2H)-one;FT-0666906;9-Benzylamino-3,4-dihydroacridin-1(2H)-one

Chemical Property of 3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone

Chemical Property:

• PSA: 45.22000
• LogP: 3.78780
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 302.141913202
• Heavy Atom Count: 23
• Complexity: 418

Purity/Quality:

97% ^*data from raw suppliers

3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=NC3=CC=CC=C3C(=C2C(=O)C1)NCC4=CC=CC=C4
• Uses: Intermediate in the preparation of Acetylcholinesterase inhibitors.

Technology Process of 3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone

There total 5 articles about 3,4-Dihydro-9-[(benzyl)amino]-1(2H)-acridinone 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: 41.0%

benzyl bromide (100-39-0) + 9-Amino-1,2,3,4-tetrahydroacridin-1-one (104675-26-5) → 9-benzylamino-3,4-dihydroacridin-1(2H)-one (104675-27-6)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; for 4h;

DOI:10.1021/jm00128a024

Reference yield:

1,3-cylohexanedione (504-02-9) → 9-benzylamino-3,4-dihydroacridin-1(2H)-one (104675-27-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 41 percent / NaOH / 4N>4> / CH₂Cl₂; H₂O / 4 h

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

DOI:10.1021/jm00128a024

Reference yield:

N-(3-oxocyclohexen-1-yl)-2-aminobenzonitrile (104675-23-2) → 9-benzylamino-3,4-dihydroacridin-1(2H)-one (104675-27-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.3 percent / K₂CO₃ / CuCl / tetrahydrofuran / 5 h / Heating

2: 41 percent / NaOH / 4N>4> / CH₂Cl₂; H₂O / 4 h

With sodium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate; copper(l) chloride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jm00128a024

upstream raw materials:

benzyl bromide

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

1,3-cylohexanedione

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

Downstream raw materials:

9-Benzylamino-1,2,3,4-tetrahydroacridin-1-ol