1-[(methyl(phenylmethyl)amino)methyl]ferrocene

Base Information

• Chemical Name: 1-[(methyl(phenylmethyl)amino)methyl]ferrocene
• CAS No.: 227805-06-3
• Molecular Formula: C₁₉H₂₁FeN
• Molecular Weight: 319.229
• Mol file: 227805-06-3.mol

Synonyms:1-[(methyl(phenylmethyl)amino)methyl]ferrocene

Chemical Property of 1-[(methyl(phenylmethyl)amino)methyl]ferrocene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1-[(methyl(phenylmethyl)amino)methyl]ferrocene

There total 3 articles about 1-[(methyl(phenylmethyl)amino)methyl]ferrocene 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: 92.0%

ferrocenecarboxaldehyde (12093-10-6) + benzyl-methyl-amine (103-67-3) → 1-[(methyl(phenylmethyl)amino)methyl]ferrocene (227805-06-3)

Guidance literature:

With trimethylamine-N-oxide; C₂₇H₂₈FeN₃O₃⁽¹⁺⁾*BF₄^(1-); hydrogen; In ethanol; at 20 ℃; for 16h; under 3750.38 Torr; chemoselective reaction; Autoclave; Inert atmosphere;

DOI:10.1021/acs.joc.9b00581

Reference yield: 75.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-benzyl-N-ferrocenylmethyl amine → 1-[(methyl(phenylmethyl)amino)methyl]ferrocene (227805-06-3)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In water; acetonitrile; sodium cyanoborohydride added to aq. formaldehyde and Fe-complex in MeCN, stirred for 30 min, CH3CO2H added dropwise, stirred at room temp. for 6 h; solvent removed, NaOH added, stirred for 30 min, extd. with Et2O, sepd.,organic layer dried over Na2SO4, column chromy. on silica gel with ethy l acetate/petroleum ether (1:5); elem. anal.;

DOI:10.1016/j.ica.2006.05.019

Reference yield: 69.0%

ferrocene (102-54-5,55404-68-7) + N,N'-dibenzyl-N,N'-dimethylmethylenediamine (1483-42-7) → 1-[(methyl(phenylmethyl)amino)methyl]ferrocene (227805-06-3)

Guidance literature:

With sodium hydroxide; phosphoric acid; In acetic acid; (under Ar, in dark); mixt. of ferrocene, ligand and H3PO4 in acetic acidheated for 5 h, cooled, diluted with H2O/Et2O 5:15, NaOH added to pH 12; extd. with CH2Cl2, organic layer dried over Na2SO4, concd., residue subjected to SiO2 column chromy. with hexane/Et2O;

DOI:10.1002/hlca.200800461

upstream raw materials:

ferrocene

N,N'-dibenzyl-N,N'-dimethylmethylenediamine

formaldehyd

ferrocenecarboxaldehyde

Downstream raw materials:

C₅H₅FeC₅H₃CH₃CH₂N(CH₃)2CH₂C₆H₅⁽¹⁺⁾*I^(1-)=[C₅H₅FeC₅H₃CH₃CH₂N(CH₃)2CH₂C₆H₅]I

rac-σPt[(η5-Cp)Fe(η5-C5H3-CH2N(methyl)-benzyl)](chloride)(DMSO)

1-formyl-2-[[methyl(phenylmethyl)amino]methyl]ferrocene