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The synthesis of the indoles 7, 15, 16 with a 3‐methoxyphenyl group, attached via an α‐side chain of 1,2,or 3 CH2 units, is reported. These compounds, after appropriate protection at C(3), were transformed into the N‐[(dimethylamino)methyl]indoles 22, 23, and 24, respectively. When treated with AcCl, these N‐Mannich bases gave, in two cases, stable N‐(chloromethyl)indoles 25 and 26. In the presence of SnCl4, ring closure occurred via electrophilic attack of 1‐methylideneindolium ions on the methoxyphenyl group. Formation of seven‐membered rings (→ 27, 28) and eight‐membered rings (→ 29) was found to be a favorable process. Cyclization to six‐membered rings did not occur within this series.

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