3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine

Base Information

• Chemical Name: 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine
• CAS No.: 13080-74-5
• Molecular Formula: C₁₄H₁₁Cl₂N
• Molecular Weight: 264.154
• Mol file: 13080-74-5.mol

Synonyms:

Chemical Property of 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine

Chemical Property:

• Melting Point: 114-115 °C
• Boiling Point: 365.9±42.0 °C(Predicted)
• Density: 1.296±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

3,?7-?Dichloro-?10,?11-?dihydro-?5H-?dibenzo[b,?f]?azepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3,?7-?Dichloro-?10,?11-?dihydro-?5H-?dibenzo[b,?f]?azepine is an intermediate in the preparation of Dichloroimipramine Hydrochloride (D434845), the analog of Imipramine Hydrochloride (I465980), a tricyclic antidepressant.

Technology Process of 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine

There total 13 articles about 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine 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: 65.0%

3,7-dichloro-10,11-dihydro-dibenzo[b,f]azepine-5-carbaldehyde → 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine (13080-74-5)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 50 - 75 ℃; for 1h; Reagent/catalyst; Inert atmosphere;

Reference yield:

2-bromo-4-chlorobenzyl bromide (33924-45-7) → 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine (13080-74-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 5 h / Heating

2: 51 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Heating

3: 94 percent / H₂, morpholine / 5 percent Rh/C / ethanol; methanol / 4 h / 18100.2 Torr / Ambient temperature

4: 79 percent / HCOONa / 3 h / Heating

5: K₂CO₃, Cu, CuBr / dimethylsulfoxide / 3 h / 160 °C

6: 5 N aq. NaOH / dimethylsulfoxide / 0.5 h / 75 °C

With morpholine; sodium hydroxide; hydrogen; sodium formate; copper; sodium hydride; potassium carbonate; copper(I) bromide; Rh on carbon; In methanol; 1,2-dimethoxyethane; ethanol; dimethyl sulfoxide;

DOI:10.1002/jhet.5570360110

Reference yield:

diethyl <(2-bromo-4-chlorophenyl)methyl>phosphonate (78347-96-3) → 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine (13080-74-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Heating

2: 94 percent / H₂, morpholine / 5 percent Rh/C / ethanol; methanol / 4 h / 18100.2 Torr / Ambient temperature

3: 79 percent / HCOONa / 3 h / Heating

4: K₂CO₃, Cu, CuBr / dimethylsulfoxide / 3 h / 160 °C

5: 5 N aq. NaOH / dimethylsulfoxide / 0.5 h / 75 °C

With morpholine; sodium hydroxide; hydrogen; sodium formate; copper; sodium hydride; potassium carbonate; copper(I) bromide; Rh on carbon; In methanol; 1,2-dimethoxyethane; ethanol; dimethyl sulfoxide;

DOI:10.1002/jhet.5570360110

upstream raw materials:

2-bromo-4-chloro-1-methyl-benzene

2-bromo-4-chlorobenzyl bromide

diethyl <(2-bromo-4-chlorophenyl)methyl>phosphonate

2-[2-(2-bromo-4-chloro-phenyl)-ethyl]-5-chloro-phenylamine