N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine

Base Information

• Chemical Name: N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine
• CAS No.: 186352-42-1
• Molecular Formula: C₁₅H₁₉NO₂
• Molecular Weight: 245.321
• Mol file: 186352-42-1.mol

Synonyms:N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine

Chemical Property of N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine

There total 5 articles about N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-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: 56.0%

tert-Butyl-[1-(6-{3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propyl}-3,4-dihydro-2H-pyridin-1-yl)-meth-(E)-ylidene]-amine (1028285-96-2) → N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine (186352-42-1)

Guidance literature:

With potassium hydroxide; In methanol; at 60 ℃; for 2h;

DOI:10.1021/jo961832b

Reference yield:

3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propan-1-ol (327155-45-3) → N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine (186352-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / I₂, imidazole, PPh₃ / benzene / 1.5 h / Ambient temperature

2: 1.) t-BuLi / 1.) Et₂O, THF, hexane, -20 deg C, 2 h, 2.) Et₂O, THF, hexane, -20 deg C, overnight

3: 56 percent / aq. KOH / methanol / 2 h / 60 °C

With 1H-imidazole; potassium hydroxide; iodine; tert.-butyl lithium; triphenylphosphine; In methanol; benzene;

DOI:10.1021/jo961832b

Reference yield:

3-<2-<(tert-butyldimethylsilyl)oxy>phenyl>-1-iodopropane (151950-83-3) → N-formyl-6-[3-(2-hydroxyphenyl)propyl]-1,2,3,4-tetrahydropyridine (186352-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) t-BuLi / 1.) Et₂O, THF, hexane, -20 deg C, 2 h, 2.) Et₂O, THF, hexane, -20 deg C, overnight

2: 56 percent / aq. KOH / methanol / 2 h / 60 °C

With potassium hydroxide; tert.-butyl lithium; In methanol;

DOI:10.1021/jo961832b

upstream raw materials:

tert-Butyl-[1-(6-{3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propyl}-3,4-dihydro-2H-pyridin-1-yl)-meth-(E)-ylidene]-amine

1-tert-butyldimethylsilyloxy-2-(2-propenyl)benzene

3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propan-1-ol

3-<2-<(tert-butyldimethylsilyl)oxy>phenyl>-1-iodopropane

Downstream raw materials:

Trifluoro-methanesulfonic acid 2-[3-(1-formyl-1,4,5,6-tetrahydro-pyridin-2-yl)-propyl]-phenyl ester