Heterocyclic compounds derived from aliphatic amines

The photolytic rearrangement of N-chloroamines derived from secondary fatty amines, such as N-methyloctadecylamine, has been investigated. The intermediate δ- or ε-chloroamines, or both, were not isolated from the reaction medium but were converted directly to their corresponding N-methyl-2-alkylpyrrolidine or piperidine analogs, or both, by treatment with alkali. The synthetic utility of this reaction has been extended to include the two functionally substituted secondary amines, N,N-dimethylazelaylamine and methyl 11-methylaminoundecanoate. The yields of isolated pure products are in the range of 50–80%. Presented at the AOCS Meeting, New York, October, 1968. ARS, USDA.