N-[2-(1H-indol-3-yl)ethyl]benzamide

Base Information

• Chemical Name: N-[2-(1H-indol-3-yl)ethyl]benzamide
• CAS No.: 4753-09-7
• Molecular Formula: C17H16N2O
• Molecular Weight: 264.327
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID601103639
• Nikkaji Number: J1.329.106C
• ChEMBL ID: CHEMBL552178
• Mol file: 4753-09-7.mol

Synonyms:N-[2-(1H-indol-3-yl)ethyl]benzamide;4753-09-7;N-(2-indol-3-ylethyl)benzamide;N-(2-(1H-indol-3-yl)ethyl)benzamide;n-benzoyltryptamine;Oprea1_089334;MLS001183962;CHEMBL552178;SCHEMBL4331421;KTEDBFKQSUUOQJ-UHFFFAOYSA-N;DTXSID601103639;HMS2849E14;MFCD00245135;STK036194;AKOS001713937;CCG-279032;MS-6917;NCGC00278566-01;SMR000502681;N-[2-(1H-indol-3-yl)-ethyl]-benzamide;AB00282286-08;EN300-22965489;SR-01000515232;SR-01000515232-1;Z26395492

Chemical Property of N-[2-(1H-indol-3-yl)ethyl]benzamide

Chemical Property:

• Melting Point: 135-137°C
• PSA: 48.38000
• LogP: 3.71520
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 264.126263138
• Heavy Atom Count: 20
• Complexity: 325

Purity/Quality:

95% ^*data from raw suppliers

N-(2-(1H-Indol-3-yl)ethyl)benzamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NCCC2=CNC3=CC=CC=C32

Technology Process of N-[2-(1H-indol-3-yl)ethyl]benzamide

There total 25 articles about N-[2-(1H-indol-3-yl)ethyl]benzamide 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: 99.0%

tryptamine (61-54-1) + benzoyl chloride (98-88-4) → N-benzoyltryptamine (4753-09-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2017.02.068

Reference yield: 99.0%

tryptamine (61-54-1) + 9-benzoyl-9H-carbazole (19264-68-7) → N-benzoyltryptamine (4753-09-7)

Guidance literature:

In tetrahydrofuran; at 30 ℃; for 24h; chemoselective reaction;

DOI:10.1246/bcsj.20200116

Reference yield: 98.0%

tryptamine (61-54-1) + benzoic acid (65-85-0,8013-63-6) → N-benzoyltryptamine (4753-09-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1111/j.1747-0285.2012.01317.x

upstream raw materials:

tryptamine

benzoyl chloride

tryptamine hydochloride

2-(benzoylamino)-3-(indol-3-yl)propanoic acid

Downstream raw materials:

1-phenyl-3,4-dihydro-9H-pyrido<3,4-b>indole hydriodide

1-nitroso-N-benzoyltryptamine

(+/-)-1-benzoyl-3a,8-dimethyl-(3ar,8ac)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole

1-phenyl-4,9-dihydro-3H-β-carboline

Refernces

• 1、 Nachtigall, Fabiane M.,Santos, Leonardo S.,Sathish, Manda. "Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement". . p. 38672 - 38677. Retrieved 2020/11/05.
• 2、 Anderson, Ryan L.,Chen, Yu,Gelis, Ioannis,Leahy, James W.,Lewandowski, Eric M.,Mccaskey, Angelica N.,Merkler, David J.,O'flynn, Brian G.,Prins, Karin Claire,Rios-Guzman, Nasha M.,Shepherd, Britney A.,Suarez, Gabriela. "Characterization of arylalkylamine n-acyltransferase from tribolium castaneum: an investigation into a potential next-generation insecticide target". . p. 513 - 523. Retrieved 2020/03/11.