Synthesis of Novel (Phenylalkyl)amines for the Investigation of StructureActivity Relationships, Part 3 : 4-Ethynyl-2,5-dimethoxyphenethylamine (=4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN)

✍ Scribed by Trachsel, Daniel (author)

• Book ID: 102255221
• Publisher: Verlag Helvetica Chimica Acta AG
• Year: 2003
• Tongue: German
• Weight: 81 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390224

✦ Synopsis

Abstract

An easy and efficient pathway for the preparation of 4‐ethynyl‐2,5‐dimethoxyphenethylamine (=4‐ethynyl‐2,5‐dimethoxybenzeneethanamine; 2C‐YN; 1) was developed, an ethynyl analogue of the potent 5‐HT~2A/C~ agonists, e.g., 4‐iodo‐2,5‐dimethoxy‐amphetamine (DOI; 2b). The ethynyl moiety was introduced by a Pd‐catalyzed Sonogashira reaction of (trimethylsilyl)ethyne with N‐(trifluoroacetyl)‐protected 4‐iodo‐2,5‐dimethoxyphenethylamine (7) in almost quantitative yield within only 1 h. Removal of the Me~3~Si group was accomplished with Bu~4~NF. Final N‐deprotection by NaOH treatment afforded the novel phenethylamine 1 in an overall yield of 88%.