The Action of Benzylamine on Aliphatic Esters

Buehler, C. A.; MacKENZIE, C. A.

doi:10.1021/ja01281a502

Cited by 8 publications

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“…45 mp 36.9–38 °C); R f 0.67 (1:20 MeOH/CH 2 Cl 2 ); 1 H NMR (400 MHz, CDCl 3 ) δ 0.96 (t, J = 7.6 Hz, 3H), 1.65–1.74 (m, 2H), 2.20 (t, J = 8.0 Hz, 2H), 4.45 (d, J = 5.6 Hz, 2H), 5.66–5.78 (br s, 1H), 7.26–7.35 (m, 5H); HRMS (ESI) 178.1238 [M + H + ] (calcd for C 11 H 15 NOH + 178.1232); Anal. (C 11 H 15 NO•0.06H 2 O): C, H, N.…”

Section: Methodsmentioning

confidence: 99%

“…Utilizing method B with 47 (2.00 mL, 21.9 mmol), NMM (3.13 mL, 28.5 mmol), IBCF (3.10 mL, 24.1 mmol), and benzylamine (2.51 mL, 23.0 mmol) gave the crude product that was recrystallized from hot EtOAc/hexanes to give the desired compound (1.18 g, 30%) as a white solid: mp 54–55 °C (lit . mp 36.9–38 °C); R f 0.67 (1:20 MeOH/CH 2 Cl 2 ); 1 H NMR (400 MHz, CDCl 3 ) δ 0.96 (t, J = 7.6 Hz, 3H), 1.65–1.74 (m, 2H), 2.20 (t, J = 8.0 Hz, 2H), 4.45 (d, J = 5.6 Hz, 2H), 5.66–5.78 (br s, 1H), 7.26–7.35 (m, 5H); HRMS (ESI) 178.1238 [M + H + ] (calcd for C 11 H 15 NOH + 178.1232); Anal.…”

Section: Methodsmentioning

confidence: 99%

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Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

et al. 2011

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Primary Amino Acid Derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to Functionalized Amino Acids (FAAs) (N′-benzyl 2- substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogs of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

et al. 2011

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Isonitrile, I. Darstellung von Isonitrilen aus monosubstituierten Formamiden durch Wasserabspaltung

1960

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Es wird tiber die Darstellungvon Isonitrilen aus monosubstituierten Formamiden durch Wasserabspaltung mittels Phosphoroxychlorids in Gegenwart von Pyridin oder Kalium-terbbutylat berichtet. An 18 Beispielen wird gezeigt, daO die Methodc allgemein anwendbar ist und auch die Darstellung von Isonitrilen erlaubt, die bisher nicht zuganglich waren. Die Konstitutionsabhiingigkeit der UV-Absorption sowie der 1R-Absorptions-Frequenzen und Intensitaten von Isonitrilen werden diskutiert.A. W. HOFMANN 1) stellte 1867 erstmals Isonitrile (I) durch Umsetzen von primaren Aminen mit Chloroform und Alkali dar.RNHz + CHC13 --R-NZC

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A facile synthesis of piperazines from primary amines

Henry

1966

Journal of Heterocyclic Chem

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A general procedure is described for converting primary amines to N-substituted piperazines. Reaction of an amine with an N-substituted iminodiacetic acid anhydride (V) yields an iminodiacetic acid monoamide (VI) which closes to a 2,6-piperazinedione (VII) upon treatment with acetic anhydride. The diones a r e reduced to piperazines with borane-THF. Fourteen examples of this process, using twelve aliphatic o r aromatic amines and three iminodiacetic acids, a r e presented. Yields of piperazines, based upon starting amine, ranged from 2 1 to 52%. The procedure is rapid and no purification problems were encountered. Alternate methods for preparing the 2,6-piperazinedione intermediates are discussed.During a synthetic program directed toward potential antimalarial agents, it was necessary to prepare several 1,4-disubstituted piperazines from a primary aromatic amine. The procedures of Prelog (2) and Pollard (3). utilizing bis(2-haloethy1)amines and bis(2 -hydroxyethy1)amines respectively, have been widely used to effect this conversion, but both proved inadequate in the present case and another was sought. Reduction of a 2,6 -piperazinedione ( e . g . , It), wherein Ra and its attached nitrogen are provided by the primary amine, appeared a PriOri to be an attractive alternate possibility. The additional five atoms of the piperazine ring would thus be provided by an iminodiacetic acid moiety ( e . g . , Ia), several of which (N-unsubstituted, N-methyl, and N-benzyl) are commercially available. Examination of the literature revealed three examples of lithium aluminum hydride reductions of such diones to piperazines (4-6) although, in each case, the goal of the work was not the incorporation of a primary amine into the ring.Chase and Downs (4) used this procedure to prepare isotopically labeled I-methylpiperazine (IIIa) by reduction of 4-methylpiperazine-2,6-dione (IIa) .The dione was obtained by fusion of N-methyliminodiacetic acid (Ia) with urea. More recently, Cignarella (5) prepared cis-2,6-dimethylpiperazine (W) by a similar reduction of 1-benzyl-cis-3, 5dimethyl-2,6-piperazinedione (IIb) followed by removal of the benzyl group by catalytic hydrogenolysis. In this case, the dione was obtained by thermal ring closure of the iminodiacetic acid monoethyl ester monobenzylamide (Ib). Both papers report excellent yields.Roderick, Platte, and

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The Action of Benzylamine on Aliphatic Esters

Abstract: 2) Garelli and Racciu, Alli acad. sci. Torino, Classe rci. lis, mal. (3) Technical monoethanolamine, boiling at 169-171 O, from Car-Vol. I, p. 114. nal., 69, I, 358-03 (1934). bide and Carbon Chemicals Corporation, was used.

Cited by 8 publications

References 0 publications

Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

Isonitrile, I. Darstellung von Isonitrilen aus monosubstituierten Formamiden durch Wasserabspaltung

A facile synthesis of piperazines from primary amines

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