(S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE

Base Information

• Chemical Name: (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE
• CAS No.: 864825-23-0
• Molecular Formula: C11H13N3
• Molecular Weight: 187.244
• Mol file: 864825-23-0.mol

Synonyms:(alphaS)-alpha-Methyl-4-phenyl-1H-imidazole-2-methanamine; (αS)-α-methyl-5-phenyl-1H-Imidazole-2-methanamine; (S)-1-(4-Phenyl-1H-Imidazol-2-Yl)Ethan-1-Amine

Chemical Property of (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE

Chemical Property:

• Boiling Point: 422.1±28.0 °C(Predicted)
• PKA: 13.16±0.10(Predicted)
• PSA: 54.70000
• Density: 1.145±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.79670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

(S)-1-(4-Phenyl-1H-imidazol-2-yl)ethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-1-(4-Phenyl-1H-imidazol-2-yl)ethanamine is an intermediate used to prepare a δ-opioid antagonists/μ-opioid agonists used in potential therapy for diarrhea-predominant irritable bowel syndrome (IBS-d).

Technology Process of (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE

There total 3 articles about (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE 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: 100.0%

benzyl [(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]carbamate (864825-21-8) → [(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amine (864825-23-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol;

DOI:10.1016/j.bmcl.2012.05.042

Reference yield: 81.0%

[(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]carbamic acid tert-butyl ester oxalate → [(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amine (864825-23-0)

Guidance literature:

[(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]carbamic acid tert-butyl ester oxalate; With sodium carbonate; In dichloromethane; water; for 2h;

With hydrogenchloride; In methanol; at 50 - 65 ℃;

Reference yield:

2-aminoacetophenone hydrochloride (5468-37-1) → [(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amine (864825-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane

2: ammonium acetate; acetic acid / 7 h / Reflux

3: palladium 10% on activated carbon; hydrogen / methanol

With 4-methyl-morpholine; palladium 10% on activated carbon; ammonium acetate; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2012.05.042

upstream raw materials:

benzyl [(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]carbamate

2-aminoacetophenone hydrochloride

Downstream raw materials:

isopropyl-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-amine

(2-(4-hydroxy-2,6-dimethyl-phenyl)-1-{isopropyl-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamoyl}-ethyl)-carbamic acid tert-butyl ester

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