Benzylamine benzamide

Isoindolines can be obtained through directed metalation reaction from N-methyl or N-phenyl benzylamines, benzamides or benzanilides. 

The comparison of the bands observed after benzonitrile and benzylamine transformation over vanadia-titania allows us to suggest that benzamide can also be obtained by oxidation of benzylamine. Moreover, the growth of the absorption near 1640 cm and the appearance of bands at 1330 and 1240 cm during benzylamine oxidation suggests that benzaldehyde is also formed. A likely assignment for the band at 1670 cm is to the stretching of a C=N double bond (75), so being likely indicative of the formation of benzaldimine. 

Die Reduktion von Benzhydroxamstiure mit Lithium-alanat in Tetrahydrofuran ergibt Benzylamin in 50% Ausbeute, wahrend die gleiche Reduktion des O-Benzoyl-Derivates von Benzhydroxamsaure, namlich N-Benzoyloxy-benzamid, 80% Ausbeute an Benzylamin neben 90% Ausbeute an Benzylalkohol ergibt3. 

Rhodium-catalyzed hydroformylation of -(substituted amino)benzyl-amines (387, X = H2) and -(substituted amino)benzamides (387, R = H, X = O) in the presence of rhodium(II) acetate dimer and triphenylphos-phine in deoxygenated ethyl acetate gave a 7 3 mixture of 1,2,3,4,4 ,5-hexahydro-6//-pyrido[l,2-a]quinazolines (388, X = H2,0) and isomeric 3-methyl-l,2,3,3fl,4,5-hexahydropyrrolo[l,2-a]quinazolines (389, X = H2, O) (94AJC1061). The methyl derivative of benzylamine 387 (R = Me, X = H2) afforded a mixture of diastereoisomers 390 and 391 (X = H2). Their ratio depended on the reaction time. Longer reaction times gave more 391 (X = H2), containing the methyl group in an equatorial position. Compound 390 isomerized into 391 (X = H2), under the aforementioned conditions. The benzamide derivative (387, R = Me, X = O) yielded only one isomer (391, X = O), independent of the reaction period. 

The reduction of benzamide to benzylamine is the illustrative example (Expt... 

N-Benzyl-2-bromo-N-methyl-benzamide (35). A suspension of morpholine resin (3, 0.63 mmol) in DCM (2 ml) was treated with. V-methyl-benzylamine (0.23 mmol) and 2-bromobenzoyl chloride (0.146 mmol). The reaction mixture was shaken for 5 h. Isocyanate resin (15, 0.2 g) was added followed by DCM (1 ml). The reaction mixture was then shaken for 16 h. Filtration of the resin followed by concentration of the filtrate gave the purified product. 

Benzamide yields only a little benzylamine benzaldhyde, which probably contained benzyl alcohol, was also formed. In a similar manner... 

Reaction with amides. Benzamides and thiobenzamides are converted to a,a-disubstituted benzylamines. Tertiary amides form ketones on reaction with RCeCl even when the reagent is present in large excess, therefore Weinreb amides are not necessary for the ketone synthesis. Enaminones are also attacked at the carbonyl group, and in the cases of a -silylated derivatives the reaction products are 3,y-unsaturated ketones. ... 

Aryl ethyl ethers are deethylai exposure to microwaves in the pres of selectivity by the addition of eth Palladium halide complexed to haloarenes with powdered NaCN ii Olefiturtions. Vinylogation 1,3-dioxolan-2-ylmethyltriphen> Ipl feasible. Similarly, asymmetric Ej been induced by RbOH in the pte Oxidations and reductions. benzylamines to benzamides with aldehydes can be carried out in tolu Epoxidation of various alken phase-transfer conditions using so economical and environmentally I a,P-epoxy ketones are deoxj H,NC(=NH)SO,H under phase-tnu... 

Oxidations and reductions. Phase-transfer catalyst enables the oxidation of benzylamines to benzamides with KMnO in an organic solvent, whereas reduction of aldehydes can be carried out in toluene using NaBH and polyethylene glycol. ... 

Sardana, S. and Madan, A.K. (2002c) Predicting anticonvulsant activity of benzamides/ benzylamines computational approach using topological descriptors. J, Comput. Aid. Mol Des., 16, 545-550. 

The second step described here is a modihed literature procedure reported by Bennet et al. [39] using benzylamine instead of diethylamine. In this method formation of benzamide by the transfer of the 5-acetyl group to benzylamine can be followed by TLC. 

Most experimental studies have supported the nondissociative mechanism (a) for this reaction,but one study reported the following results the polyphos-phoric acid (PPA)-catalyzed Beckmann rearrangement of pinacolone oxime produced N-f-butylacetamide, while the PPA-catalyzed rearrangement of 2-methyl-2-phenylpropiophenone oxime produced N-benzoyl-a, -dimethyl-benzylamine and benzamide. Carrying out the rearrangement on a mixture of pinacolone oxime and 2-methyl-2-phenylpropiophenone oxime produced the products expected from each reactant, plus Af-f-butylbenzamide and N-acetyl-a,a-dimethylbenzylamine. 

Katritzky, A.R., Lapucha, A.R. and Siskin, M., Aqueous high-temperature chemistry of carbo- and heterocycles. 12. Benzonitriles and pyridinecarbonitriles, benzamides and pyridinecarboxamides, and benzylamines... 

Benzamide heated 15 min. with 1.1 moles POCI3 at 60-90 on a water bath, cooled to 0-5 , a suspension of a 5-fold excess of Zn-powder in abs. ethanol added, and heated again ca. 15 min. on a water bath benzylamine. Y 70%. -Similarly N-Cyclohexylbenzamide N-cyclohexylbenzylamine. Y 90%. -Benzopiperidide N-benzylpiperidine. Y 90%. F. e. s. A. Basha and Atta-ur-Rahman, Experientia 33, 101 (1977) with NaBH4 instead of Zn, also reduction of lactams, s. M. E. Kuehne and P. J. Shannon, J. Org. Chem. 42, 2082 (1977). 

The optimized Mo(CO)6-based aminocarbonylation protocol was applied in the synthesis of a variety of benzamides. Both electron-rich and electron-poor aryl iodides proved to be efficient coupling partners. In the set of amines examined in this reaction, the previously investigated piperidine produced improved yields. Furthermore, aniline and benzylamine also reacted easily. The sterically hindered... 

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