You may recall that NaBH 4 is used for the reduction of aldehydes and ketones. To refresh yourself on the mechanism, hover here and an image will pop up ( link).Īfter the imine is formed, it must be reduced to the amine. It’s possible to use the familiar reducing agent sodium borohydride (NaBH 4) for this process. We covered imine formation previously ( See article: Imines – Properties, Reactions, Mechanisms). This is a much more controlled manner of forming nitrogen-carbon bonds. Once the imine is formed, the C=N bond can be reduced, giving us a new alkyl group attached to nitrogen. While alkylation can happen multiple times on an amine, imines only form once on a given amine. Separating mixtures is fine on paper, but (trust me on this) it can be a real a pain in practice. Yes, you could try and separate out the secondary amine that’s formed from the tertiary amine, but we’re not going to settle for 10-30% yields here. methyl iodide, CH 3I ) will result in significant formation of the undesired tertiary amine (i.e. How do you do it?ĭirect treatment of benzylamine with an alkylating agent (e.g. Say you have a primary amine such as benzylamine and would like to make N-methylbenzylamine. How Do We Make This Amine, If Direct Alkylation Doesn’t Work?
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