Tiracizine

Base Information

• Chemical Name: Tiracizine
• CAS No.: 83275-56-3
• Molecular Formula: C₂₁H₂₅N₃O₃
• Molecular Weight: 367.448
• UNII: 9UUO2T61K7
• DSSTox Substance ID: DTXSID5048714
• Nikkaji Number: J397.474J
• Wikipedia: Tiracizine
• Wikidata: Q6586877
• NCI Thesaurus Code: C75137
• Metabolomics Workbench ID: 154426
• ChEMBL ID: CHEMBL1625260
• Mol file: 83275-56-3.mol

Synonyms:3-carbethoxyamido-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenz(b,f)azepine HCl;3-carbethoxyamino-5-dimethylaminoacetyl-2,2'-iminodibenzyl HCl;AWD 19166;AWD-19-166;Bonnecor;GS 015;GS 105;GS-015;GS-105;tiracizine

Chemical Property of Tiracizine

Chemical Property:

• Melting Point: 127-128 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 525.3 °C at 760 mmHg
• PKA: 13.42±0.20(Predicted)
• Flash Point: 271.5 °C
• PSA: 61.88000
• Density: 1.215 g/cm³
• LogP: 3.71790
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 367.18959167
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

98%Min ^*data from raw suppliers

TIRACIZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)NC1=CC2=C(CCC3=CC=CC=C3N2C(=O)CN(C)C)C=C1

Technology Process of Tiracizine

There total 4 articles about Tiracizine 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: 76.0%

3-carbethoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenzazepine (78816-66-7) + dimethyl amine (124-40-3) → 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenzazepine (83275-56-3)

Guidance literature:

In water; toluene; for 1.5h; Heating;

DOI:10.1007/BF00766590

Reference yield:

3-amino-10,11-dihydro-5H-dibenzazepine (10464-35-4) → 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenzazepine (83275-56-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Na₂CO₃ / acetone; H₂O / 1.5 h

2: toluene / 4 h / Heating

3: toluene / 4 h / 70 - 110.8 °C

With sodium carbonate; In water; acetone; toluene;

Reference yield:

3-amino-5-acetyl-10,11-dihydro-5H-dibenzazepine (84803-67-8) → 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenzazepine (83275-56-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / KOH / propan-1-ol / 5 h / Heating

2: 91 percent / 20percent aq. KOH / acetone / 1 h / Heating

3: 97 percent / toluene / 2 h / Heating

4: 76 percent / toluene; H₂O / 1.5 h / Heating

With potassium hydroxide; In propan-1-ol; water; acetone; toluene;

DOI:10.1007/BF00766590

upstream raw materials:

3-carbethoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenzazepine

dimethyl amine

3-amino-10,11-dihydro-5H-dibenzazepine

3-carbethoxyamino-10,11-dihydro-5H-dibenzazepine

Downstream raw materials:

3-amino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenzazepine

[5-(2-Dimethylamino-acetyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-3-yl]-carbamic acid ethyl ester; hydrochloride

Refernces

• 1、 Wunderlich,Stark,Carstens,Lohmann,Grizenko,Skoldinov. "New derivatives of 10,11-dihydro-5H-dibenz[b,f]azepins with antiarrhythmic efficacy". . p. 827 - 830. Retrieved 2007/10/02.