N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine

Base Information

• Chemical Name: N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine
• CAS No.: 130081-94-6
• Molecular Formula: C14H16 N2 O
• Molecular Weight: 228.294
• DSSTox Substance ID: DTXSID80156332
• Nikkaji Number: J1.328.403B
• Wikidata: Q83024384
• ChEMBL ID: CHEMBL45765
• Mol file: 130081-94-6.mol

Synonyms:N-methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine;NMPHMI

Chemical Property of N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine

Chemical Property:

• Vapor Pressure: 4.7E-07mmHg at 25°C
• Boiling Point: 402.5°Cat760mmHg
• Flash Point: 197.2°C
• PSA: 28.40000
• Density: 1.05g/cm³
• LogP: 1.94890
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 228.126263138
• Heavy Atom Count: 17
• Complexity: 309

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C=C(C=C2)O)C=C1CN(C)CC#C

Technology Process of N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine

There total 3 articles about N-Methyl-N-(2-propynyl)-2-(5-hydroxy-1-methylindolyl)methylamine 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: 75.0%

1-methyl-2-((methylamino)methyl)-1H-indol-5-ol (130081-92-4) + propargyl bromide (106-96-7) → 5-hydroxy-N-[(1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine (130081-94-6)

Guidance literature:

With tert-butylamine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm501501a

Reference yield:

5-benzyloxy-1-methyl-2-(methylaminomethyl)indole (133845-54-2) → 5-hydroxy-N-[(1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine (130081-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, AcOH / 10percent Pd/C / 5 h / 760 Torr / Ambient temperature; other hydrogen source and reaction conditions

2: t-BuNH₂ / tetrahydrofuran / Ambient temperature

With hydrogen; acetic acid; tert-butylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0223-5234(91)90210-E

Reference yield:

N-methyl-2-(5-methoxyindolyl)methylamine (91180-69-7) → 5-hydroxy-N-[(1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine (130081-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: boron tribromide / dichloromethane; chloroform / 48 h / -78 - 20 °C / Inert atmosphere

2: tert-butylamine / tetrahydrofuran / 0 - 20 °C

With boron tribromide; tert-butylamine; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1021/jm501501a

upstream raw materials:

1-methyl-2-((methylamino)methyl)-1H-indol-5-ol

propargyl bromide

5-benzyloxy-1-methyl-2-(methylaminomethyl)indole

N-methyl-2-(5-methoxyindolyl)methylamine

Downstream raw materials:

N-((5-((1-benzylpiperidin-4-yl)methoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine

N-{[5-(2-(1-benzylpiperidin-4-yl)ethoxy)-1-methyl-1H-indol-2-yl]methyl}-N-methylprop-2-yn-1-amine

N-((5-(3-(4-benzylpiperazine-1-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine

N-{[5-(3-(4-benzylpiperidin-1-yl)propoxy)-1-methyl-1H-indol-2-yl]methyl}-N-methylprop-2-yn-1-amine

Refernces

• 1、 Bautista-Aguilera, Oscar M.,Samadi, Abdelouahid,Chioua, Mourad,Nikolic, Katarina,Filipic, Slavica,Agbaba, Danica,Soriano, Elena,De Andrés, Lucía,Rodríguez-Franco, María Isabel,Alcaro, Stefano,Ramsay, Rona R.,Ortuso, Francesco,Ya?ez, Matilde,Marco-Contelles, José. "N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a new cholinesterase and monoamine oxidase dual inhibitor". supporting information. p. 10455 - 10463. Retrieved 2015/02/19.