Studies of the N-Oxides of N,N-Dialkylamino Acids. II. The Syntheses of N,N-Dialkylglycine and Corresponding N-Oxides

Abstract

Abstract The reductive condensations of glycine with various aliphatic straight-chain aldehydes, such as acetaldehyde, propionaldehyde, and n-butyraldehyde, give the corresponding N,N-dialkyl derivatives. The N-monoalkyl derivative has not been obtained in any case. In another type of reactions, those with aliphatic branched-chain aldehydes, such as isobutyraldehyde and isovaleraldehyde, considerable N-monoalkylation takes place besides the dialkylation. The oxidations of N,N-dialkylglycine to the corresponding N-oxides have been successfully performed using an aqueous mixture of hydrogen peroxide and acetic acid except in the case of N,N-diisobutylglycine. Similar reductive condensations of sarcosine with various aliphatic aldehydes, such as acetaldehyde, propionaldehyde, n- and iso-butyraldehyde, and isovaleraldehyde, gave the corresponding N-alkylsarcosines. N-Isobutyl and N-isoamyl sarcosine were also obtained by the methylation of the corresponding N-monoalkylglycine. The N-oxides of N-alkylsarcosine were synthesized by a procedure similar to that described above.