2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine

Base Information

• Chemical Name: 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine
• CAS No.: 69718-72-5
• Molecular Formula: C11H13N
• Molecular Weight: 159.231
• UNII: R5BK32EZX6
• Wikipedia: 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine
• Mol file: 69718-72-5.mol

Synonyms:1,5-Methano-3-benzazepane;R5BK32EZX6;UNII-R5BK32EZX6;2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine;1,5-Methano-2,3,4,5-tetrahydro-1H-3-benzazepine;SCHEMBL13916010;AKOS006306548

Chemical Property of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 277.937 °C at 760 mmHg
• Flash Point: 128.894 °C
• PSA: 74.78000
• Density: 1.07 g/cm³
• LogP: 4.51200
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 159.104799419
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99.3% ^*data from raw suppliers

10-AZA-TRICYCLO[6.3.1.0]DODECA-2,4,6-TRIENE BENZAZAPINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CNCC1C3=CC=CC=C23
• Isomeric SMILES: C1[C@@H]2CNC[C@H]1C3=CC=CC=C23

Technology Process of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine

There total 7 articles about 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine 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: 95.0%

C11H7NO3 → 10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-triene (69718-72-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 6h; Solvent; Reagent/catalyst; Cooling with ice;

Reference yield:

3-benzyl-2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine hydrochloride → 10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-triene (69718-72-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 24h; under 2068.59 - 2585.74 Torr;

DOI:10.1055/s-2004-829135

Reference yield:

2-indanone (615-13-4) → 10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-triene (69718-72-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic acid; bromine / 2 h / 25 °C / Cooling with ice

2.1: ethanol; water / 5 h / 20 °C

3.1: potassium hydroxide; water / ethanol / 4 h / 75 °C

4.1: acetic anhydride / 5 h / 100 °C

4.2: 3 h / 75 °C

5.1: sodium tetrahydroborate / tetrahydrofuran / 6 h / 20 °C / Cooling with ice

With sodium tetrahydroborate; water; bromine; acetic anhydride; acetic acid; potassium hydroxide; In tetrahydrofuran; ethanol; water;

upstream raw materials:

2-indanone

1,3-dibromo-indan-2-one

Downstream raw materials:

1-(10-aza-tricyclo[6.3.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

2,3,4,5-tetrahydro-1,5-methylene-1H-3-benzazepine hydrochloride

Refernces

• 1、 -. "Preparation method of varenicline key intermediate". . . Retrieved 2019/04/04.
• 2、 -. "Nicontinic acetylcholine receptor antagonists in the treatment of restless legs syndrome". . . Retrieved 2008/06/13.