(E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine

Base Information

• Chemical Name: (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine
• CAS No.: 181648-53-3
• Molecular Formula: C₁₃H₁₈ClNO
• Molecular Weight: 239.745
• Mol file: 181648-53-3.mol

Synonyms:(E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine

Chemical Property of (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine

There total 11 articles about (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine 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%

(E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]carbamic acid ethyl ester (181648-40-8) → (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine (181648-53-3)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 48h; Heating;

DOI:10.1021/jo960673t

Reference yield:

4-Chloro-3-methylphenol (59-50-7) → (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine (181648-53-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / imidazole / dimethylformamide

2: 66 percent / NBS, benzoyl peroxide / CCl₄ / 2 h / Heating

3: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -35 deg C, 3 h

4: 94 percent / LiAlH₄ / diethyl ether / 1.5 h

5: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

6: 95 percent / tetrahydrofuran / 2 h

7: 96 percent / propionic acid / 1.) reflux, 1 h, 2.) 160 deg C, 1 h

8: 1.) KOH, 2.) imidazole / 1.) MeOH, H₂O, room temperature, 4 h, 2.) DMF, 25 deg C, overnight

9: 1.) Et₃N, (PhO)2P(O)N₃ / 1.) dioxane, room temperature, 30 min; reflux, 40 min, 2.) reflux, overnight

10: 63 percent / KF / dimethylformamide / 27 h

11: 100 percent / KOH / ethanol; H₂O / 48 h / Heating

With 1H-imidazole; potassium fluoride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; Perbenzoic acid; oxalyl dichloride; diphenyl phosphoryl azide; dimethyl sulfoxide; propionic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo960673t

Reference yield:

tert-butyl-(4-chloro-3-methyl-phenoxy)-dimethyl-silane (181648-42-0) → (E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]amine (181648-53-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 66 percent / NBS, benzoyl peroxide / CCl₄ / 2 h / Heating

2: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -35 deg C, 3 h

3: 94 percent / LiAlH₄ / diethyl ether / 1.5 h

4: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

5: 95 percent / tetrahydrofuran / 2 h

6: 96 percent / propionic acid / 1.) reflux, 1 h, 2.) 160 deg C, 1 h

7: 1.) KOH, 2.) imidazole / 1.) MeOH, H₂O, room temperature, 4 h, 2.) DMF, 25 deg C, overnight

8: 1.) Et₃N, (PhO)2P(O)N₃ / 1.) dioxane, room temperature, 30 min; reflux, 40 min, 2.) reflux, overnight

9: 63 percent / KF / dimethylformamide / 27 h

10: 100 percent / KOH / ethanol; H₂O / 48 h / Heating

With 1H-imidazole; potassium fluoride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; Perbenzoic acid; oxalyl dichloride; diphenyl phosphoryl azide; dimethyl sulfoxide; propionic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo960673t

upstream raw materials:

(E)-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]carbamic acid ethyl ester

4-Chloro-3-methylphenol

tert-butyl-(4-chloro-3-methyl-phenoxy)-dimethyl-silane

[3-(bromomethyl)-4-chlorophenoxy](tert-butyl)dimethylsilane

Downstream raw materials:

(E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-2,5-pyrrolidinedione

(E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone

Refernces