Alkylation benzyl methylamine

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). ... 

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]. 

The synthetic concept is simple. Benzyl cyanide is alkylated twice with /5 -bis-(chloroethyl)methylamine, and the nitrile function transformed into the ethyl ester in a Pinner reaction with ethanol... 

The ortho-ester functionalized polymers can be hydrolyzed to the corresponding carboxyl functionalized polymers. Similarly, fimctionalization with the oxiranes, glycidylpropyltrimethoxysilane, 3,4-epoxy-l-butene, and 1,1,1-trifluoro-2,3-epoxypropane has been investigated (195) to prepare trimethoxysilyl functionalized polymers, 1,3-diene fiinctionalized macromonomers, and trifluoromethyl functionalized polsrmers, respectively. Secondary amine functionalized polymers were prepared by termination with iV-(benzylidene)methylamine and also using an iV-benzyl tertiary amine functionalized alkyl lithimn initiator followed by hy-drogenolysis of the benzyl group. 

The Fukuyama synthesis commenced with the copper-catalyzed asymmetric reduction of butenolide 26 to give lactone 27 in 98% enantiomeric excess (Scheme 9). Sequential alkylation with CbzCl followed by methyl acrylate provided lactone 28 and installed both of the required contiguous stereocenters. The key Curtius rearrangement was performed by conversion of the benzyl ester to the acyl azide followed by heating. Subsequent treatment with aqueous HCI provided cyclized lactam 8. This compound was then dibromi-nated to lactam 29 using bromine, ZnCl2, and formic acid, which were the only conditions that were able to introduce the orf/to-bromine. The fully elaborated aromatic compound 29 was treated with methylamine followed by PDC to obtain cyclic A -methylimide 23. 

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