11-Piperazinyldibenzo[b,e][1,4]diazepine

Base Information

• Chemical Name: 11-Piperazinyldibenzo[b,e][1,4]diazepine
• CAS No.: 56296-18-5
• Molecular Formula: C17H18N4
• Molecular Weight: 278.35
• Mol file: 56296-18-5.mol

Synonyms:DREADD 21;DREADD agonist 21;11-(1-Piperazinyl)-5H-dibenzo[b,e][1,4]diazepine;5H-Dibenzo[b,e][1,4]diazepine, 11-(1-piperazinyl)-;

Chemical Property of 11-Piperazinyldibenzo[b,e][1,4]diazepine

Chemical Property:

• Boiling Point: 470.1±55.0 °C(Predicted)
• PKA: 8.56±0.10(Predicted)
• PSA: 39.66000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 2.56740

Purity/Quality:

99%min. ^*data from raw suppliers

DREADDAgonist21 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DREADD agonist 21 activates hM3Dq (EC50 = 1.7 nM), a designer receptor exclusively activated by designer drugs (DREADD) derived from the human muscarinic acetylcholine M3 receptor. It does not agonize the hM3 receptor and displays relatively weaker binding affinities for serotonin 5-HT2A, 5-HT2C, α1A-adrenergic, and histamine H1 receptors (Kis = 66, 170, 280, and 6 nM, respectively).
• Uses: DREADD agonist 21 is an agonist of hM3Dq, a designer receptor exclusively activated by designer drugs (DREADD). It preferentially binds hM3Dq?DREADDs over endogenous hM3?receptors.

Technology Process of 11-Piperazinyldibenzo[b,e][1,4]diazepine

There total 9 articles about 11-Piperazinyldibenzo[b,e][1,4]diazepine 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: 63.0%

piperazine (110-85-0) + 5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one (5814-41-5) → 11-(piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine (56296-18-5)

Guidance literature:

piperazine; With titanium tetrachloride; In methoxybenzene; Inert atmosphere; Large scale reaction;

5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one; In methoxybenzene; at 50 - 110 ℃; Large scale reaction;

DOI:10.1155/2011/212014

Reference yield: 63.0%

piperazine (110-85-0) + 11-chloro-5H-dibenzo[b,e][1,4]diazepine (50373-21-2) → 11-(piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine (56296-18-5)

Guidance literature:

In toluene; Reflux;

DOI:10.1021/cn500325v

Reference yield:

N-(2-nitrophenyl)anthranilic acid (5933-35-7) → 11-(piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine (56296-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / N,N-dimethyl-formamide / 2 h / 3620.13 Torr / Large scale reaction

2.1: sulfuric acid / N,N-dimethyl-formamide / Reflux; Large scale reaction

3.1: titanium tetrachloride / methoxybenzene / Inert atmosphere; Large scale reaction

3.2: 50 - 110 °C / Large scale reaction

With sulfuric acid; hydrogen; titanium tetrachloride; In methoxybenzene; N,N-dimethyl-formamide;

DOI:10.1155/2011/212014

upstream raw materials:

piperazine

5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one

N-(2-nitrophenyl)anthranilic acid

anthranilic acid

Refernces

• 1、 Kalhapure, Rahul S.,Patil, Bhushan P.,Jadhav, Mahantesh N.,Kawle, Laxmikant A.,Wagh, Sanjay B.. "Synthesis of 11-(Piperazin-1-yl)-5H-dibenzo[b,e] [1,4]diazepine on kilo scale". experimental part. p. 1747 - 1749. Retrieved 2012/05/07.
• 2、 -. "USE OF N-DESMETHYLCLOZAPINE AND RELATED COMPOUNDS AS DOPAMINE STABILIZING AGENTS". Page/Page column 74. . Retrieved 2010/11/24.