N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine
• CAS No.: 218900-31-3
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.326
• Mol file: 218900-31-3.mol

Synonyms:N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine

Chemical Property of N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine

There total 8 articles about N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine 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: 82.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-methoxy-N-methylbenzylamine (702-24-9) → N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine (218900-31-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201801524

Reference yield: 73.0%

1-bromo-4-methoxy-benzene (104-92-7) + tert-butyl N,N-dimethylcarbamate (7541-17-5) → N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine (218900-31-3)

Guidance literature:

tert-butyl N,N-dimethylcarbamate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -60 ℃; for 1h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at -60 - 20 ℃; for 1.5h; Inert atmosphere;

1-bromo-4-methoxy-benzene; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; PtBu₃*HBF₄; In toluene; at 40 ℃; for 17h; Inert atmosphere;

DOI:10.1002/anie.201310904

Reference yield:

N-(tert-butoxycarbonyl)sarcosine (13734-36-6) → N-(tert-butoxycarbonyl)-N-methyl(p-methoxybenzyl)amine (218900-31-3) + N-(t-butoxycarbonyl)-N-methyl(o-methoxybenzyl)amine

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / 16 h / 20 °C / Electrochemical reaction

With triethylamine; In acetonitrile; 2: |Friedel-Crafts Alkylation;

DOI:10.1039/d0sc03701j

upstream raw materials:

di-tert-butyl dicarbonate

1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride

1-bromo-4-methoxy-benzene

tert-butyl N,N-dimethylcarbamate

Refernces

• 1、 Choi, Geunho,Hong, Soon Hyeok. "Selective Monomethylation of Amines with Methanol as the C1 Source". supporting information. p. 6166 - 6170. Retrieved 2018/04/30.
• 2、 Yoshida, Suguru,Igawa, Kazunobu,Tomooka, Katsuhiko. "Nucleophilic substitution reaction at the nitrogen of arylsulfonamides with phosphide anion". . p. 19358 - 19361. Retrieved 2013/02/22.