The Synthesis of Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some Ring-methoxylated 1-Amino-and 2-Aminoindanes
Ronald T. Coutts, Jerry L. Malicky
Canadian Journal of Chemistry February 1, 1974 DOI: 10.1139/v74-061 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Key points | Reports synthetic routes to 2-amino-4,7-dimethoxy-5-methylindane (12a), a cyclic analog of the hallucinogen DOM, via a trans-aminoindanol intermediate; one route through the oxime gave the product in low yield, while direct catalytic reduction also yielded the cis-aminoindanol byproduct. Additional aminoindane derivatives are described. |
Abstract
The synthesis of 2-amino-4,7-dimethoxy-5-methylindane (12a), the cyclic analog of the known hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), is described. The key intermediate was trans-2-amino-4,7-dimethoxy-6-methyl-1-indanol (trans-10a) which was converted to 12a in two ways. The prolonged action of hydrochloric acid on trans-10a gave 4,7-dimethoxy-5-methyl-2-indanone (11d), the oxime of which, on catalytic reduction, was converted to 12a in low yield. A direct catalytic reduction of trans-10a in the presence of hydrochloric acid also gave 12a, together with cis-2-amino-4,7-dimethoxy-6-methyl-l-indanol (cis-10a).The synthesis and properties of other derivatives of 2-aminoindane, and some derivatives of 1-amino-indane are also described.