trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide

Base Information

• Chemical Name: trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide
• CAS No.: 106680-78-8
• Molecular Formula: C₁₅H₁₄N₂O₃
• Molecular Weight: 270.288
• Mol file: 106680-78-8.mol

Synonyms:

Chemical Property of trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide

There total 5 articles about trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide 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: 55.2%

5-carbamoyl-10,11-dihydro-11-oxo-5H-dibenzazepine-10-yl acetate (113952-21-9) → cis-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide (58955-94-5,58955-93-4) + trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide (106680-78-8,58955-93-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 2 ℃; for 1.5h;

DOI:10.1002/hlca.19870700730

Reference yield:

trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzoazepine-5-carbonyl chloride (106680-75-5) → trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide (106680-78-8,58955-93-4)

Guidance literature:

With ammonia; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00388a004

Reference yield:

1a,10b-dihydro-6H-dibenzooxirenoazepine-6-carbonyl chloride (41359-09-5) → trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide (106680-78-8,58955-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / 0.5 M aq. HClO₄ / tetrahydrofuran / 7 h / 45 °C

2: 0.13 g / NH₃ (g) / methanol / 2 h / Ambient temperature

With perchloric acid; ammonia; In tetrahydrofuran; methanol;

DOI:10.1021/jm00388a004

upstream raw materials:

trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzoazepine-5-carbonyl chloride

5-carbamoyl-10,11-dihydro-11-oxo-5H-dibenzazepine-10-yl acetate

1a,10b-dihydro-6H-dibenzooxirenoazepine-6-carbonyl chloride

dibenzoazepine

Refernces

• 1、 Belluci, Giuseppe,Berti, Giancarlo,Chiappe, Cinzia,Lippi, Annalisa,Marioni, Franco. "The Metabolism of Carbamazepine in Humans: Steric Course of the Enzymatic Hydrolysis of the 10,11-Epoxide". . p. 768 - 773. Retrieved 2007/10/02.