Halo ketones, amination reaction, with alcohols

Next, a nucleophilic substitution reaction at saturated carbon. a-Halo ketones are excellent electrophiles and react rapidly with nucleophiles, such as this secondary amine, by the S 2 mechanism (Chapter 17). All that remains is to reduce the ketone and the acid to alcohols and remove the benzyl protecting group (both discussed in Chapter 24). 

The interaction of alkyl halides, preferably iodides or bromides, with hexamine in chloroform or alcohol solution forms quaternary ammonium salts which on heating with hydrochloric acid are readily converted to primary amines. The procedure has been employed successfully in the reaction of primary, but not secondary or tertiary, aliphatic halides, certain benzyl halides, halo ketones, halo acids, and halo esters. The yields range from 40% to 85%. 

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