Synthesis of 7‐Alkoxy/Hydroxy‐α‐methyltryptamines

Abstract

A simple method for the preparation of 7‐alkoxy/hydroxy‐α‐methyl‐DL‐tryptamines is reported. The key steps of the synthesis are the Japp–Klingemann coupling of 2‐piperidone‐3‐carboxylic acid 3 with diazonium salts 4, the Fischer‐type cyclization of hydrazones 5 to β‐carboline derivatives 6 and their hydrolysis to title compounds 8.

Keywords:

• 7‐Methoxy‐α‐methyltryptamine
• 7‐Hydroxy‐α‐methyltryptamine
• 7‐Benzyloxy‐α‐methyltryptamine
• Japp–Klingemann coupling
• Reductive amination

Acknowledgments

The authors gratefully acknowledge the support from Glenmark Research Centre. The authors thank Dr. B. Gopalan for his suggestions on the subject. The authors also wish to thank Dr. Vinod R. Uchil and Mr. Machhindra Gund for their technical help.