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%.