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A new synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5‐tetrahydro‐1H‐3‐benzazepines is described. Suitably substituted phenethylamines and their α‐methyl homologs in the form of their N‐acetyl derivatives are chloromethylated, the resulting benzyl chlorides are reacted with cyanide and hydrolysis of the latter yields 2‐(2‐aminoethyl)phenylacetic acid derivatives. Thermal cyclization yields the corresponding lactams. Hydride reduction of these lactams furnishes the substituted 2,3,4,5‐tetrahydro‐1H‐3‐benzazepines which may be methylated on nitrogen by formaldehyde and hydrogen. By this sequence a number of previously unde‐scribed compounds have been prepared.

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Chloromethylation of N‐acetyl‐2,3,4,5‐tetrahydro‐7,8‐methylenedioxy‐1H‐3‐benzazepine (4) proceeded, depending on reaction conditions, at the 6‐ or 6,9‐ positions. Subsequent transformation of these intermediates provided a series of mono and bis aromatic‐substituted derivatives of the parent benzazepine 3.

The nitration of 2,3,4,5‐tetrahydro‐1H‐3‐benzazepine and its 3‐methyl and 3‐acetyl derivatives yields the corresponding 7‐nitro derivatives which can be further transformed by classical procedures. The preparation of the ether cleavage products of the known 2,3,4,5‐tetrahydro‐7,8‐dimethoxy‐1H‐3‐benzazepine is also reported.