N-benzyl-1-pentyl-1H-indole-3-carboxamide

Base Information

• Chemical Name: N-benzyl-1-pentyl-1H-indole-3-carboxamide
• CAS No.: 695213-59-3
• Molecular Formula: C21H24N2O
• Molecular Weight: 320.434
• UNII: MM02A5A302
• DSSTox Substance ID: DTXSID501009997
• Nikkaji Number: J3.667.554C
• Wikipedia: SDB-006
• Wikidata: Q15410205
• Mol file: 695213-59-3.mol

Synonyms:695213-59-3;N-benzyl-1-pentyl-1H-indole-3-carboxamide;SDB-006;1H-Indole-3-carboxamide, 1-pentyl-N-(phenylmethyl)-;N-benzyl-1-pentylindole-3-carboxamide;UNII-MM02A5A302;MM02A5A302;OLACYTSBFXCDOH-UHFFFAOYSA-N;DTXSID501009997;STK734901;AKOS001729980;J3.667.554C;1-Pentyl-N-(phenylmethyl)-1H-indole-3-carboxamide;1H-Indole-3-carboxylic acid, 1-pentyl-, benzylamide;Q15410205

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Chemical Property of N-benzyl-1-pentyl-1H-indole-3-carboxamide

Chemical Property:

• PSA: 37.52000
• LogP: 5.33630
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 320.188863393
• Heavy Atom Count: 24
• Complexity: 391

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCN1C=C(C2=CC=CC=C21)C(=O)NCC3=CC=CC=C3

Technology Process of N-benzyl-1-pentyl-1H-indole-3-carboxamide

There total 6 articles about N-benzyl-1-pentyl-1H-indole-3-carboxamide 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: 84.0%

1-pentyl-1H-indole-3-carbonyl chloride (1338925-23-7) + benzylamine (100-46-9) → 1-pentyl-N-(phenylmethyl)-1H-indole-3-carboxamide (695213-59-3)

Guidance literature:

With triethylamine; In dichloromethane; for 14h; Inert atmosphere;

DOI:10.1021/cn400035r

Reference yield:

indole (120-72-9) → 1-pentyl-N-(phenylmethyl)-1H-indole-3-carboxamide (695213-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

3.1: potassium hydroxide / toluene; methanol / 2 h / Inert atmosphere; Reflux

4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Inert atmosphere

5.1: triethylamine / dichloromethane / 14 h / Inert atmosphere

With oxalyl dichloride; sodium hydride; triethylamine; N,N-dimethyl-formamide; potassium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/cn400035r

Reference yield:

1-pentyl-1H-indole (59529-21-4) → 1-pentyl-N-(phenylmethyl)-1H-indole-3-carboxamide (695213-59-3)

Guidance literature:

Multi-step reaction with 4 steps

1: mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

2: potassium hydroxide / toluene; methanol / 2 h / Inert atmosphere; Reflux

3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Inert atmosphere

4: triethylamine / dichloromethane / 14 h / Inert atmosphere

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; potassium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/cn400035r

upstream raw materials:

indole

1-pentyl-1H-indole

1-Bromopentane

N-pentyl-3-trifluoroacetylindole