633290-71-8Relevant academic research and scientific papers
Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships: Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (=4-ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN)
Trachsel, Daniel
, p. 2754 - 2759 (2003)
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-HT2A/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 Me3Si group was accomplished with Bu4NF. Final N-deprotection by NaOH treatment afforded the novel phenethylamine 1 in an overall yield of 88percent.
