Benzyl methylamine

Methyl benzyl amine Chlorate. See Benzyl-methylamine Chlorate, above... 

Benzyl methylamine QH5CH2-NHCH3 68.7+2 287.4 + 8.4 VLPP 1972GOL/SOL... 

Numerous syntheses of racemic fluoxetine are reported. Consider the retrosynthesis and then propose the synthesis starting with the Mannich reaction and benzyl methylamine as the amino component. 

Methamphetannne is a notorious street drug One synthesis involves reductive amination of benzyl methyl ketone with methylamine What is the structure of methamphetamine ... 

The (ZZ-ephedrine was resolved into its components by the use of d-and Z-mandelic acids. In 1921 Neuberg and Hirsch showed that benz-aldehyde was reduced by yeast, fermenting in suerose or glueose solution to benzyl aleohol and a phenylpropanolone, which proved to be Z-Ph. CHOH. CO. CH3. This ean be simultaneously, or consecutively, eondensed with methylamine and then eonverted to Z-ephedrine by reduction, e.g., with aluminium amalgam in moist ether, or by hydrogen in presenee of platinic oxide as catalyst (Knoll, Hildebrant and Klavehn ). 

Reduction of phenylacetone in the presence of methylamine rather than ammonia gives methamphetamine (53), an agent similar in action to the primary amine. Alkylation of 53 with benzyl chloride affords the analog, benzphetamine (54). ... 

Diethanol methylamine Sodium amide Sulfuric acid Hydrogen chloride Thionyl chloride Benzyl cyanide Ethanol ... 

The C-H insertion a to nitrogen can be extended to acyclic systems. The reaction with jY-benzyl-iV-methylamine is an excellent example of the interplay between steric and electronic effects. The benzylic position would be electronically the most activated, but due to the steric crowding, the C-H insertion occurred exclusively at the iV-methyl site (Equation (27)).86 This is a general method for generating a-aryl-/5-amino acid derivatives. The N,N-dimethylamino group undergoes a very favorable C-H insertion by the donor/acceptor-substituted carbenoids. Indeed, the reaction is so favorable that double C-H insertion was readily achieved to form the elaborated -symmetric amine 10 (Equation (28)).87... 

In addition to amino-methylamine exchanges, amino-benzylamine exchanges were found. When iv-benzyl salts of pyrimidine, 4,6-dimethyl-pyrimidine, and 4-t-butylpyrimidine react with liquid ammonia, the respective debenzylated compounds were isolated (Scheme III.9) (82JHC3739). 

The starting diol was transformed into the dibromide by elemental bromine with triphenyl phosphine adduct which undergoes the Arbuzov-Michaelis reaction under somewhat drastic conditions at 150 °C (step a). Catalytic removal of the benzyl group was performed by a Pd/C catalyst (step b) and the alcohol formed was allowed to react with dichloropurine in the presence of triphenylphosphine and diethylazodicarboxylate (Mit-sunobu reaction) (step c). Finally the desired product was obtained by reaction with methylamine (step d) and the removal of ethyl groups at the phosphorus centre was performed by transilylation using trimethyliodosilane (step e). 

Meperidine Meperidine, the ethyl ester of l-methyl-4-phenylpiperidine-4-carboxyhc acid (3.1.39), is a synthetic opioid analgesic. Its synthesis is accomphshed by the alkylation of benzyl cyanide using Af,Al-fcix-(2-chlorethyl)-iV-methylamine in the presence of sodium amide, which forms l-methyl-4-phenyl-4-cyanopiperidine (3.1.38), and its subsequent acidic ethanolysis into meperidine [30-32]. 

Die N-Allylierung von primaren Aminen (Methylamin, Benzylamin) kann, neben vielen anderen Moglichkeiten, auch in der Weise vorgenommen werden, daB man die Amine durch Reaktion mit Phosphorsaure-chlorid-diethylester bzw. Thiophosphorsaure-chlorid-0,0-diethylester phosphoryliert, die Produkte mit Allyl-bromid in die N-phosphorylierten sekundaren Allylamine iiberfuhrt und diese Verbindungen mittels 2 N Salzsaure zu Allyl-methyl- bzw. Allyl-benzyl-amin spaltet1. 

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