1,4-ditosyl-1,4-diazepane

Base Information

• Chemical Name: 1,4-ditosyl-1,4-diazepane
• CAS No.: 5769-35-7
• Molecular Formula: C19H24N2O4S2
• Molecular Weight: 408.543
• Mol file: 5769-35-7.mol

Synonyms:1,4-Bis-(toluol-4-sulfonyl)-hexahydro-[1,4]diazepin;hexahydro-1,4-bis(p-tolylsulfonyl)-1H-1,4-diazepine;1H-1,4-Diazepine, hexahydro-1,4-bis(p-tolylsulfonyl)-;Perhydro-1,4-di-p-toluolsulfonyl-1,4-diazepin;

Chemical Property of 1,4-ditosyl-1,4-diazepane

Chemical Property:

• Melting Point: 149-150 °C
• Boiling Point: 576.1±60.0 °C(Predicted)
• PKA: -5.73±0.20(Predicted)
• PSA: 91.52000
• Density: 1.303±0.06 g/cm3(Predicted)
• LogP: 4.42610
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1,4-Ditosyl-1,4-diazepane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,4-Ditosyl-1,4-diazepane is a derivative Fasudil(F150023). Fasudil is a protein kinase A inhibitor and may be used in medicinal combinations for hepatitis treatment.

Technology Process of 1,4-ditosyl-1,4-diazepane

There total 6 articles about 1,4-ditosyl-1,4-diazepane 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: 88.1%

ethylenediamine (107-15-3,85404-18-8) + 1.3-chlorobromopropane (109-70-6) + p-toluenesulfonyl chloride (98-59-9) → N,N'-di-p-toluenesulfonylhomopiperazine (5769-35-7)

Guidance literature:

ethylenediamine; 1.3-chlorobromopropane; p-toluenesulfonyl chloride; With sodium hydroxide; In butan-1-ol; Reflux; Large scale;

With sodium hydroxide; In butan-1-ol; for 2.5h; pH=12; Reflux; Large scale;

Reference yield:

2-[(3-aminopropyl)amino]ethanol (4461-39-6) → N,N'-di-p-toluenesulfonylhomopiperazine (5769-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane; Raney nickel; hydrogen / 200 °C / 14710.2 Torr

With 1,4-dioxane; hydrogen; nickel;

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → N,N'-di-p-toluenesulfonylhomopiperazine (5769-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 4 h / 20 °C

2: sodium hydride

With sodium hydride; sodium hydroxide;

DOI:10.1021/acs.oprd.1c00211

upstream raw materials:

1,4-Diazacycloheptane

2-[(3-aminopropyl)amino]ethanol

ethylenediamine

1.3-chlorobromopropane

Downstream raw materials:

1,4-Diazacycloheptane

fasudil hydrochloride

N,N'-Ditosyl-5-methyl-hexahydro-1,4-diazepin

2-methyl-1,4-bis-(toluene-4-sulfonyl)-[1,4]diazepane