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6944933 
Journal Article 
Gabriel Synthesis of Hexakis(aminomethyl)benzene and Its Derivatization 
Masuda, J; Kondo, S; Matsumoto, Y; Yamanaka, M; , 
2018 
ChemistrySelect
ISSN: 2365-6549 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
3 
22 
6112-6115 
English 
WOS:000435260800012 
Hexakis(aminomethyl)benzene, which is a key precursor for various hexa-substituted functional molecules, was synthesized by Gabriel synthesis. Nucleophilic substitution of hexakis(bromomethyl)benzene with potassium phthalimide gave hexakis(phthalimidemethyl)benzene in excellent yield. Hydrazinolysis of the phthalimide moieties of hexakis(phthalimidemethyl)benzene afforded a mixture of hexakis(aminomethyl)benzene and 2,3-dihydrophthalazine-1,4-dione. Pure hexakis(aminomethyl)benzene was isolated as its hexahydrochloride upon treating the mixture with HCl. Hexakis-amides and hexakis-tosylamide were prepared from hexahydrochloride of hexakis(aminomethyl)benzene in good to high yields. Alkyl-substituted hexakis-amide shows extremely high solubility in non-polar organic solvents like chloroform and n-hexane. Density functional theory calculation of the structure of hexakis-amide show that all substituents were oriented to the same side (aaaaaa conformation) via intramolecular hydrogen bonding. 
amides; amines; Gabriel synthesis; hydrogen bonds; synthetic methods