8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride

Base Information

• Chemical Name: 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride
• CAS No.: 1272663-25-8
• Molecular Formula: C₂₂H₂₅NO₂*ClH
• Molecular Weight: 371.907
• Mol file: 1272663-25-8.mol

Synonyms:8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride

Chemical Property of 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride

There total 6 articles about 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride 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: 50.0%

phenylacetaldehyde (122-78-1) + 3β-benzoyloxy-8-azabicyclo[3.2.1]octane (18470-33-2,20811-95-4,123202-90-4) → 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride (1272663-25-8)

Guidance literature:

phenylacetaldehyde; 8-azabicyclo[3.2.1]octan-3α-yl benzoate; With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In diethyl ether; water;

DOI:10.1021/ja110571r

Reference yield:

3β-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane (1272720-51-0) → 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride (1272663-25-8)

Guidance literature:

With hydrogenchloride; In diethyl ether;

DOI:10.1016/j.bmcl.2011.12.008

Reference yield:

3β-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane → 8-phenethyl-8-azabicyclo[3.2.1]octan-3α-yl benzoate hydrochloride (1272663-25-8)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / toluene / 4 h / Reflux

2: 1,2-dichloro-ethane / 19 h / Cooling with ice; Inert atmosphere; Reflux

3: methanol / 22 h / 20 °C / Reflux

4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 48 h / 20 °C / Inert atmosphere

5: hydrogenchloride / diethyl ether

With hydrogenchloride; sodium tris(acetoxy)borohydride; triethylamine; In methanol; diethyl ether; 1,2-dichloro-ethane; toluene;

DOI:10.1016/j.bmcl.2011.12.008

upstream raw materials:

phenylacetaldehyde

3β-benzoyloxy-8-azabicyclo[3.2.1]octane

3β-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane

tropinone

Refernces

• 1、 Edink, Ewald,Rucktooa, Prakash,Retra, Kim,Akdemir, Atilla,Nahar, Tariq,Zuiderveld, Obbe,Van Elk, Rene,Janssen, Elwin,Van Nierop, Pim,Van Muijlwijk-Koezen, Jacqueline,Smit, August B.,Sixma, Titia K.,Leurs, Rob,De Esch, Iwan J. P.. "Fragment growing induces conformational changes in acetylcholine-binding protein: A structural and thermodynamic analysis". supporting information; experimental part. p. 5363 - 5371. Retrieved 2011/06/11.