Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride

Base Information

• Chemical Name: Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride
• CAS No.: 73038-10-5
• Molecular Formula: C21H28ClN3O6
• Molecular Weight: 453.9165
• DSSTox Substance ID: DTXSID50993812
• ChEMBL ID: CHEMBL1202418
• Mol file: 73038-10-5.mol

Synonyms:N(sup 1),N(sup 8)-Bis(2,3-dihydroxybenzoyl)spermidine monohydrochloride;N(sup 1),N(sup 8)-Bis(2,3-dihydroxybenzoyl)spermidine hydrochloride hydrate;2,3-Dihydroxy-N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)benzamide HCl H2O;N-(3-((4-((2,3-Dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxybenzamide HCl;73038-10-5;Benzamide, 2,3-dihydroxy-N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-, hydrochloride, hydrate;Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride;74427-44-4;C21H27N3O6.ClH;C21H27N3O6.xClH.H2O;CHEMBL1202418;DTXSID50993812;C21-H27-N3-O6.Cl-H;C21-H27-N3-O6.x-Cl-H.H2O;LS-26520;LS-26521;N-{3-[(4-{[(2,3-Dihydroxyphenyl)(hydroxy)methylidene]amino}butyl)amino]propyl}-2,3-dihydroxybenzene-1-carboximidic acid--hydrogen chloride (1/1)

Chemical Property of Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride

Chemical Property:

• Vapor Pressure: 1.7E-19mmHg at 25°C
• Boiling Point: 686.8°Cat760mmHg
• Flash Point: 369.2°C
• Density: g/cm³
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 453.1666633
• Heavy Atom Count: 31
• Complexity: 535

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)O)C(=O)NCCCCNCCCNC(=O)C2=C(C(=CC=C2)O)O.Cl

Technology Process of Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride

There total 12 articles about Benzamide, N-(3-((4-((2,3-dihydroxybenzoyl)amino)butyl)amino)propyl)-2,3-dihydroxy-, monohydrochloride 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: 65.0%

2,3-bis(benzyloxy)-N-(3-(4-(2,3-bis(benzyloxy)benzamido)butylamino)propyl)benzamide (74272-81-4) → N1,N8-bis(2,3-dihydroxybenzoyl)spermidine hydrochloride (73038-10-5,74427-44-4)

Guidance literature:

With hydrogenchloride; formic acid; palladium on activated charcoal;

Reference yield:

2,3-Dihydroxybenzoic acid (303-38-8) → N1,N8-bis(2,3-dihydroxybenzoyl)spermidine hydrochloride (73038-10-5,74427-44-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / H₂SO₄ / 20 h / Heating

2: 98 percent / K₂CO₃ / dimethylformamide / Ambient temperature

3: 83 percent / 40percent KOH / H₂O; tetrahydrofuran

4: dicyclohexylcarbodi-imide/DMAP / CHCl₃ / Ambient temperature

5: 79 percent / CH₂Cl₂ / 3 h / Ambient temperature

6: 65 percent / HCO₂H-MeOH/HCl / Pd-C

With hydrogenchloride; dmap; potassium hydroxide; formic acid; sulfuric acid; potassium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

Reference yield:

N-(2-Cyanoethyl)-N-(3-cyanopropyl)-benzylamine (1216-04-2) → N1,N8-bis(2,3-dihydroxybenzoyl)spermidine hydrochloride (73038-10-5,74427-44-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / LiAlH₄/AlCl₃ / diethyl ether / 18 h

2: 1,8-bis(dimethylamino)naphthalene / CH₂Cl₂ / 20 h / Ambient temperature

3: H₂ / PdO / acetic acid

4: NaOMe / methanol

With lithium aluminium tetrahydride; aluminium trichloride; hydrogen; sodium methylate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trimethyleneglycol; In methanol; diethyl ether; dichloromethane; acetic acid;

DOI:10.1021/jo01297a008

upstream raw materials:

2,3-bis(benzyloxy)-N-(3-(4-(2,3-bis(benzyloxy)benzamido)butylamino)propyl)benzamide

methyl-2,3-dihydroxybenzoate

2,3-Dihydroxybenzoic acid

2,3-dibenzyloxybenzoic acid

Downstream raw materials:

3-<(2,3-dihydroxybenzoylamino)propyl>-N-<4-(2,3-dihydroxy-benzoylamino)butyl>-2-hydroxybenzoyl-glycylamide