1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Base Information

• Chemical Name: 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS No.: 32407-75-3
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45
• Mol file: 32407-75-3.mol

Synonyms:1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Chemical Property of 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

There total 6 articles about 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 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: 23.0%

7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (78495-54-2) + 4-chloro-1,2-dimethoxybenzene (16766-27-1) → 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (32407-75-3)

Guidance literature:

7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; With sec.-butyllithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Inert atmosphere;

4-chloro-1,2-dimethoxybenzene; With sec.-butyllithium; In tetrahydrofuran; pentane; at -78 - 20 ℃; regioselective reaction;

DOI:10.1055/s-0034-1380453

Reference yield: 14.0%

1-(α-hydroxy-3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (17052-75-4) → 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (32407-75-3) + 5-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3-dihydro-1H-3-benzazepine (32407-74-2)

Guidance literature:

In formic acid; for 24h; Heating;

Reference yield:

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (16620-96-5) → 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (32407-75-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 2 h / Reflux; Inert atmosphere

2.1: sodium hydride / 1,4-dioxane / Inert atmosphere; Reflux

3.1: sodium tetrahydroborate / methanol / 5 h / 65 °C

4.1: sec.-butyllithium / tetrahydrofuran; pentane / 1 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C

With sodium tetrahydroborate; sec.-butyllithium; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; pentane;

DOI:10.1055/s-0034-1380453

upstream raw materials:

1-(α-hydroxy-3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

4-chloro-1,2-dimethoxybenzene