1-phenethyl-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: 1-phenethyl-1,2,3,6-tetrahydropyridine
• CAS No.: 92039-54-8
• Molecular Formula: C13H17N
• Molecular Weight: 187.285
• Mol file: 92039-54-8.mol

Synonyms:1-phenethyl-1,2,3,6-tetrahydropyridine

Chemical Property of 1-phenethyl-1,2,3,6-tetrahydropyridine

Chemical Property:

• PSA: 3.24000
• LogP: 2.42890

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(2-Phenylethyl)-1,2,3,6-tetrahydropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-phenethyl-1,2,3,6-tetrahydropyridine

There total 6 articles about 1-phenethyl-1,2,3,6-tetrahydropyridine 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: 87.0%

1-(2-phenylethyl)pyridinium bromide (6324-18-1) → 1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine (92039-54-8)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 1.5h;

DOI:10.1007/s10593-020-02748-8

Reference yield: 80.1%

1-(2-phenylethyl)pyridinium chloride (29871-24-7) → 1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine (92039-54-8)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 4h;

DOI:10.1002/rcm.4673

Reference yield: 71.0%

1,2,3,6-tetrahydropyridine (694-05-3) + 1-phenyl-2-bromoethane (103-63-9) → 1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine (92039-54-8)

Guidance literature:

DOI:10.1002/ardp.19903230211

upstream raw materials:

1,2,3,6-tetrahydropyridine

1-phenyl-2-bromoethane

pyridine

1-(2-phenylethyl)pyridinium bromide

Downstream raw materials:

1-phenethylpyridin-2(1H)-one

phenylacetaldehyde

1-phenethyl-3,4-epoxypiperidine

1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine N-oxide

Refernces

Transformations of 1-phenethyl-1,2,3,6-tetrahydropyridines in the presence of trifluoromethanesulfonic acid

10.1007/s10593-020-02748-8

Vera A. Shadrikova et al. investigate the synthesis of benzomorphan analogs through the intramolecular Friedel–Crafts reaction of 1-phenethyl-1,2,3,6-tetrahydropyridines catalyzed by trifluoromethanesulfonic acid (TfOH). The study aims to develop more potent and less addictive opiate alkaloid analogs by focusing on the benzomorphan nucleus. The researchers synthesized 1,2,3,6-tetrahydropyridines from 1-phenethylpyridinium bromides via reduction and then reacted them with TfOH to produce azatricyclic structures. The direction of the reaction and the resulting structures were influenced by the position of the substituent relative to the multiple bond in the tetrahydropyridine. The structures of the synthesized compounds were confirmed through spectral analysis methods, including IR, 1H NMR, 13C NMR, and GC-MS. The study demonstrated that unsubstituted or 4-methyl substituted tetrahydropyridines yielded 1,4,5,6-tetrahydro-2H-3,6-ethano[3]benzazocines, while 5-methyl substituted tetrahydropyridines produced 7-methyl1,2,4,5,6,7-hexahydro-3,7-methano[3]benzazonines.