N-methyl-benzylamine

A mixture of 23.8 grams (0.2 mol) of propargyl bromide, 24.2 grams (0.2 mol) of N-methyl benzylamine and 400 ml of anhydrous ethanol in the presence of 42.4 grams (0.4 mol) of anhydrous sodium carbonate was heated at the boiling temperature and under reflux for a period of 17 hours. 

Dioxo-4,8-diphenyl-l,3,5,7-tetraaza-bicyclof3.3.0]octan laBt sich durch Lithium-alanat in5-Hydroxy-3- phenyl-1,2,4- triazolidin (14% d.Th.), N-Methyl- benzylamin auf-spalten4 ... 

The synthesis and purification of C12BMG by the reaction of N-methyl-benzylamine with sodium chloroacetate followed by the quaternization of the resulting tertiary ammonioacetate with 1-bromododecane is described elsewhere (12). Purification of aqueous solutions of the surfactant for surface tension measurements and determination of the surface tension of the solutions by the Wilhelmy method using a sandblasted platinum blade were by techniques previously described (13). The concentration of C12BMG in aqueous solution was determined by measuring its absorbance at 263 nm (e = 350.5). 

Reduction of the complex on Raney nickel yielded benzylamine, N-methyl-benzylamine, and N,N-dimethylbenzylamine but no / -phenylbenzylamine, a reduction product resulting under the same reaction conditions from benzyl cyanide. Hydrolysis with dilute sulfuric acid in acetic acid yielded benzylamine only, and oxidation of the complex with potassium permanganate gave 4.2 moles of benzoic acid per mole of complex. The bromide anion can be exchanged metathetically with various other anions such as perchlorate, iodide, and thiocyanate. When heated at 100° C. in vacuum, the complex lost one mole of benzyl bromide and yielded only one dicyanotetrakis(benzylisonitrile)iron(II) complex. 

To the solution of 16.2 g thereof in 450 ml of ethanol, 14.10 g of N-methyl-benzylamine are added and the mixture is refluxed for 3 hours. It is evaporated, the residue taken up in methylene chloride, the solution washed with saturated aqueous sodium carbonate dried, filtered and evaporated. The residue is triturated with diethyl ether, to yield the l-(o-nitrobenzyl)-2-(N-methyl-N-benzylaminoacetyl)pyrrole. 

Benzyloxy-4-methoxy-benzaldehyd wird zu 22% aus dem entspreehenden N-Methyl-benzylamin und Sauerstoff in Gegenwart von Kupfer(I)-chlorid erhalten126 ... 

Then, we have investigated the cleavage of allylcarbamates (Table 2). The reaction was first conducted on primary amines in homogeneous medium. Under treatment with mol 2 % of Pd(0) catalyst and 2.2 eq. of nucleophile N-Allocbenzyl-amine 7 was quantitatively cleaved to recover the parent molecule within 10 minutes (entry 1). However, when N-allyloxycarbonyl-N-methyl benzylamine 8 was allowed to react under the same conditions, the undesired reaction of N-allylation... 

The catalytic system can be recycled up to 10 times as presented in the following scheme (the procedure is applied on N-methyl N-allyloxycarbonyl benzylamine), without loss of efficiency. After completion of the reaction, the first schlenck tube containing the free amine in the organic layer and the catalyst in the aqueous layer is linked, by a siphon tube, to another schlenck tube containing the protected amine dissolved in butyronitrile. The aqueous layer with the active catalyst is transferred under argon pressure into the second tube, over the fresh solution of N-allyloxycarbonyl-N-methyl benzylamine. 

This material is a mixture of dl-diamine meso-diamine N-methyl-benzylamine (approximately 82.6 4.4 13.0) as shown by1H NMR (see Note 8). 

Benzylamine, o-chloro-N-(cyanomethyl)-N-methyl-isoindole synthesis from, 4, 323 Benzylisoquinoline alkaloids synthesis, 1, 446 Benzynes... 

Benzyl alcohol, o-methyl-, 34, 58 Benzylamine, 35, 91 Benzylamine, 2,3-dimethoxy-N-methyl, 30, 59 N,N,o-trimethyl-, 34, 61... 

The benzylamine counterpart (as if one were to move the amine function from the beta-carbon to the alpha-carbon of the three carbon chain of the amphetamine molecule) is alpha-ethyl-3,4-methylenedioxybenzylamine or l-amino-l-(3,4-methylenedioxyphenyl)propane, ALPHA. The hydrochloride salt has a mp of 199-201 °C. At low threshold levels (10 milligram area) there were eyes-closed dreams with some body tingling. The compound was not anorexic at any dose (up to 140 milligrams) and was reported to produce a pleasant, positive feeling. It is very short-lived (about 3 hours). The N-methyl homologue is alpha-ethyl-N-methyl-3,4-methylenedioxybenzylamine or 1 -methylamino-1 -(3,4-methylenedioxy-phenyl)propane, M-ALPHA. It is similar in action, but is perhaps twice as potent (a plus one or plus two dose is 60 milligrams) and of twice the duration,... 

The 2-benzazepin-3-ones 259 have been made in moderate yields by sequential intramolecular acid-catalyzed addition followed by thiol elimination from the precursor phenylsulfanylacrylamides 258 (Scheme 33). The acrylamides 258 were prepared from reaction of the benzylamines 255 with the PNB-ester 256 to give the amides 257, and then N-methylation with Mel in the presence of potassium hydroxide and tetraethylammonium bromide, as a phase-transfer catalyst. Other noncyclized products were also observed depending on the structure of the A-aryl methyl group in 258 and on the nature of the solvent <2002H(57)1063>. 

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. 

Carbon-13 n.m.r. spectroscopy has been used to study benzylisoquinoline and tetrahydroisoquinoline alkaloids and their JV-methyl quaternary salts.30 N-Benzylpapaverinium bromide has been shown to undergo aerial oxidation in alkaline solution to 2-benzyl-6,7-dimethoxyisoquinolone and to give bases of general structure (10) with methylamine, benzylamine, and pyrrolidine.31 Chlorosulphonation of papaverinol affords the sulphonic acid ester (11), mild hydrolysis of which yields the acid (12), which with diazomethane is esterified and dehydrated to (13).32 N-Methyl-l,2-dihydropapaverine has been shown by kinetic studies and orbital-symmetry requirements to rearrange to the salt (14) by the route previously postulated.33... 

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