exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile

Base Information

• Chemical Name: exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile
• CAS No.: 1003194-36-2
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.348

Synonyms:exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile

Chemical Property of exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile

Chemical Property:

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Technology Process of exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile

There total 3 articles about exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile 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:

3-chloro-8-methyl-8-azabicyclo[3.2.1]octane + 4-Bromophenylacetonitrile (16532-79-9) → exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile (1003194-36-2)

Guidance literature:

3-chloro-8-methyl-8-azabicyclo[3.2.1]octane; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; hexane; for 2h; Heating;

With zinc dibromide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.25h;

4-Bromophenylacetonitrile; bis(acetylacetonate)nickel(II); In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 25 ℃; for 72h; Further stages.;

DOI:10.1021/ol702499h

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) + 3-chloro-8-methyl-8-azabicyclo[3.2.1]octane (2292-12-8) → exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile (1003194-36-2)

Guidance literature:

3-chloro-8-methyl-8-azabicyclo[3.2.1]octane; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

With zinc dibromide; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

4-Bromophenylacetonitrile; With bis(acetylacetonate)nickel(II); bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; at 25 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jo201630e

Reference yield:

3-tropanol (120-29-6) → exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile (1003194-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / chloroform / 19 h / -30 °C / Inert atmosphere; Reflux

1.2: Inert atmosphere

2.1: diisobutylaluminium hydride; magnesium; lithium chloride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux

2.2: 0.25 h / 20 °C / Inert atmosphere

2.3: 72 h / 25 °C / Inert atmosphere

With thionyl chloride; diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; chloroform; 2.3: Negishi coupling reaction;

DOI:10.1021/jo201630e

upstream raw materials:

4-Bromophenylacetonitrile

3-chloro-8-methyl-8-azabicyclo[3.2.1]octane

3-tropanol

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