Birkofer, Leonhard published the artcileRegularities in the hydrogenative fission of N-benzyl compounds, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1942), 429-41, database is CAplus.
Because of the value of the preparative method of the catalytic removal of the N-CH2Ph group, a study has been made of the influence of the residue on the N atom upon catalytic debenzylation. All hydrogenations were carried out at room temperature and atm. pressure in EtOH or AcOH, using PdO or PtO2 as catalyst. PhCH2NH2, (PhCH2)2NH and PhCH2NHMe are unchanged in the presence of PdO. (PhCH2)3N in AcOH (PdO) or its HCl salt in H2O (PdO) gives 97% of (PhCH2)2NH.HCl; the amine is not reduced by Na and EtOH. Methylcetylbenzylamine in AcOH (PdO) gives 92% of cetylmethylamine-HCl and lauryldibenzylamine gives laurylmethylamine. Dodecyldibenzylamine in AcOH (PtO2) gives 84% of dodecylhexahydrobenzylamine-HCl, m. 218°. (PhCH2)2NNH2 in absolute EtOH (PdO) yields 88% of PhCH2NHNH2; tetrabenzyltetrazene [(PhCH2)2NN:]2 gives (PhCH2)2NH. (PhCH2)3MeNOH with PdO in EtOH readily yields PhCH2NHMe (flavianate, m. 190°; picrolonate, m. 210°), whereas (PhCH2)3MeNI is not reduced. PhCH2NPhMe2Cl gives 90% of cyclohexyldimethylamine. 2-Benzyldihydroisoindole in EtOH (PdO) yields 75% of 1,3-dihydroisoindole, b3 100°. 1,4-Dibenzylpiperazine in AcOH (PdO) gives 92% of piperazine diacetate, m. 234°. α-Monobenzylaminotetrazole gives aminotetrazole. PhCH2NH2 (1 mol.) in AcOEt is treated with a concentrated aqueous solution of 4 mols. of KCN and then dropwise with 1.1 mols. of Br in AcOEt at 5-10°, and the AcOEt solution shaken with 30% NaOH; the alkali removes the benzylcyanamide, which is polymerized to tribenzylisomelamine (1,3,5-tribenzyl-2,4,6-triimino-1,3,5-triazine) (I), m. 129-30°; short heating with HCl gives NH3; with H and PdO in EtOH this yields melamine. The elimination of PhCH2 from 2-imino-1-benzyl-1,2-dihydropyridine is slow and incomplete and is accompanied by nuclear hydrogenation, the products being 2-amino-3,4,5,6-tetrahydropyridine and 2-imino-1-benzylpiperidine (picrate, m. 106°). 2-Benzylaminopyridine does not lose PhCH2 but is hydrogenated to 2-benzylamino-3,4,5,6-tetrahydropyridine, m. 40-1° (picrate, yellow, m. 131°; picrolonate, yellow, m. 199°). Aromatic rings, CO2H and CN groups activate the compounds so that PhCH2 is removed from a sec-N atom. PhNHCH2Ph in EtOH (PdO) gives 97.5% of PhNH2 and PhMe, whereas PtO2 gives mainly cyclohexylhexahydrobenzylamine and small amounts of cyclohexylamine and hexahydrotoluene. PhN(CH2Ph)2 with PdO in EtOH gives 89% of PhNH2 and PhMe. 2-(Dibenzylamino)naphthalene in AcOH (PdO) gives 88% of 2-C10H7NH2 and PhMe. ClCH2CO2H (9 g.) and 40 g. (PhCH2)2NH in 20 cc. dioxane, heated 5 h. at 120°, give 82% of N,N-dibenzylglycocoll, m. 200°; Me ester, m. 41°; hydrogenation in AcOH (PdO) or in EtOH (PdO) gives NH2CO2H (95%) or its Me ester (96%). (PhCH2)2NCN yields NCNH2 or I because of polymerization of PhCH2NHCN if hydrogenation is interrupted before it is complete. (CONHCH2Ph)2 and N,N-dibenzylurethane, b2 169°, b4 181° (82% yield), are stable toward H.
Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Recommanded Product: N,N-Dibenzylcyanamide.
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