A Modified Emde Degradation. Reductive Cleavage of Quaternary Ammonium Salts by Raney Nickel.

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Abstract
A modified Emde degradation, in which a combination of Raney nickel alloy and sodium hydroxide solution was used as the reduction agent in place of sodium amalgam in the original Emde reaction, was applied to four open-chain quaternary salts (I to IV) to give the corresponding des-N products and trimethylamine in a good yield as summarized in Table I. Degradation of cyclic bases, such as phenanthridine and its 6-methyl derivative, by this modified method also proceeded smoothly under the same conditions as above to form the corresponding des-N compounds (VIII and XIV) via dihydromethine bases (VI and XIII). So far as these experiments were concerned, the cleavage was effected usually with a better yield of the products and under milder working conditions than those of the original method.

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