Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-

Base Information

• Chemical Name: Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-
• CAS No.: 521059-17-6
• Molecular Formula: C16H27NO2Si
• Molecular Weight: 293.481
• DSSTox Substance ID: DTXSID00432589
• Nikkaji Number: J2.096.557F
• Pharos Ligand ID: JRGV3Z6JVLBA
• ChEMBL ID: CHEMBL2204341
• Mol file: 521059-17-6.mol

Synonyms:Rac-Sila-Venlafaxine;CHEMBL2204341;521059-17-6;Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-;SCHEMBL6383395;DTXSID00432589;BDBM50462113;1-[alpha-(Dimethylaminomethyl)-4-methoxybenzyl]silacyclohexane-1-ol

Chemical Property of Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 293.181105638
• Heavy Atom Count: 20
• Complexity: 284

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC(C1=CC=C(C=C1)OC)[Si]2(CCCCC2)O

Technology Process of Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-

There total 6 articles about Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]- 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: 86.0%

1-chloro-1-[1-(4-methoxyphenyl)vinyl]-1-silacyclohexane (781626-14-0) + dimethyl amine (124-40-3) → rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol (521059-17-6)

Guidance literature:

dimethyl amine; With n-butyllithium; In tetrahydrofuran; hexane; at -50 - -25 ℃; for 1.53333h;

1-chloro-1-[1-(4-methoxyphenyl)vinyl]-1-silacyclohexane; In tetrahydrofuran; hexane; at -40 - 20 ℃; for 4h;

Reference yield: 86.0%

{1-[2-dimethylamino-1-(4-methoxy-phenyl)-ethyl]-silinan-1-yl}-dimethyl-amine (521059-16-5) → rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol (521059-17-6)

Guidance literature:

With potassium acetate; acetic acid; In hexane; at 0 ℃; for 1h; pH=5;

DOI:10.1016/j.bmcl.2005.12.062

Reference yield:

1,1-dichloro-1-silacyclohexane (2406-34-0) → rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol (521059-17-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium; 1,2-bis(dimethylamino)ethane / hexane / 72 h / 20 °C

1.2: hexane / 6 h / 20 °C

1.3: 66 percent / hexane / 16 h / 20 °C

2.1: n-butyllithium; 2,4,6-triisopropylbenzenesulfonylhydrazone; 1,2-bis(dimethylamino)ethane / hexane / -78 - 20 °C

2.2: 47 percent / hexane / 16 h / 20 °C

3.1: 77 percent / HCl / diethyl ether / 0.17 h / 0 °C

4.1: n-buthyllithium / hexane; tetrahydrofuran / 1.5 h / -50 - -25 °C

4.2: hexane / -40 - 20 °C

5.1: 86 percent / potassium acetate; aq. acetic acid / hexane / 1 h / 0 °C / pH 5

With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 2,4,6-triisopropylbenzenesulfonylhydrazone; potassium acetate; acetic acid; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1016/j.bmcl.2005.12.062

upstream raw materials:

{1-[2-dimethylamino-1-(4-methoxy-phenyl)-ethyl]-silinan-1-yl}-dimethyl-amine

1,1-dichloro-1-silacyclohexane

1-chloro-1-[1-(4-methoxyphenyl)vinyl]-1-silacyclohexane

1-methoxy-1-(2,4,6-trimethoxyphenyl)-1-silacyclohexane