6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine

Base Information

• Chemical Name: 6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine
• CAS No.: 5768-55-8
• Molecular Formula: C8H12N2
• Molecular Weight: 136.197
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50437403
• Nikkaji Number: J603.918I
• Wikidata: Q82252893
• Mol file: 5768-55-8.mol

Synonyms:6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine;5768-55-8;1,2-pentamethyleneimidazole;5H-Imidazo[1,2-a]azepine,6,7,8,9-tetrahydro-;SCHEMBL173406;DTXSID50437403;MBVCARRYXQUTLF-UHFFFAOYSA-N;MFCD11870772;AKOS015907673;SY310363;CS-0143362;FT-0646349;A831557

Chemical Property of 6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 297.222 °C at 760 mmHg
• Flash Point: 133.555 °C
• PSA: 17.82000
• Density: 1.139 g/cm³
• LogP: 1.60950
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

98%Min ^*data from raw suppliers

6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=NC=CN2CC1

Technology Process of 6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]azepine

There total 6 articles about 6,7,8,9-Tetrahydro-5H-imidazo[1,2-a]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: 79.9%

caprolactam (105-60-2,9012-16-2) + 2,2-diethoxy-ethanamine (645-36-3) → 2,3,4,6,7,8,9,10-octahydropyrimido<1,2-a>azepino (5768-55-8)

Guidance literature:

tin(IV) chloride; In dichloromethane; 1,3,5-trimethyl-benzene; for 45h; Heating;

DOI:10.1021/jo00096a066

Reference yield: 63.0%

1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole (191542-42-4) → 2,3,4,6,7,8,9,10-octahydropyrimido<1,2-a>azepino (5768-55-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 5h; Heating;

DOI:10.1016/S0040-4039(97)00740-5

Reference yield:

1-chloro-5-iodopentane (60274-60-4) → 2,3,4,6,7,8,9,10-octahydropyrimido<1,2-a>azepino (5768-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium borohydride / 1) ethanol, 0 deg C, 30 min; 2) ethanol, rt, 16 h

2: 64 percent / sodium iodide / acetone / 18 h / Heating

3: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h

4: 63 percent / Bu₃SnH, AIBN / toluene / 10 h / Heating

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; sodium iodide; In acetone; toluene;

DOI:10.1016/S0040-4020(99)00104-0

upstream raw materials:

caprolactam

2,2-diethoxy-ethanamine

1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole

1-chloro-5-iodopentane

Downstream raw materials:

3-bromo-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepine

1-(4-Fluorophenyl)piperazine

C₈H₁₀N₂O

Refernces

• 1、 Aldabbagh, Fawaz,Bowman, W. Russell. "Radical cyclisation onto imidazoles and benzimidazoles". . p. 3793 - 3794. Retrieved 2007/10/03.
• 2、 Maffrand,Frehel,Eloy,et al.. "Synthesis and pharmacological activity of new heterocyclic compounds: imidazole and triazole polycondensated derivatives". . p. 528 - 532. Retrieved 2007/10/05.