Synthesis of 5-hydroxy-[6-14C]-methyl-2-di-n-propylaminotetralin

  title={Synthesis of 5-hydroxy-[6-14C]-methyl-2-di-n-propylaminotetralin},
  author={D. L. Koble and Lawrence J. Fischer},
  journal={Journal of Labelled Compounds and Radiopharmaceuticals},
By an improved synthesis, 5-hydroxy-6-methyl-2-di-n-propylaminotetralin (DK-118), a dopamine agonist, has been obtained in only six steps and in greater than 10% overall yield. This new synthesis has been used for the preparation of 5-hydroxy-[6-14C]-methyl-2-di-n-propylaminotetralin (I) to be used in metabolic studies. The 14C-radiolabel was introduced near the end of the synthesis by an ortho-specific formylation procedure using 14C-paraformaldehyde. 
1 Citations
Synthesis of R‐(+)‐ and S‐(−)‐8‐hydroxy‐2‐(N, N‐dipropylamino)‐[2‐3H] tetralin. HCl (8‐OH‐DPAT) a 5HT1A receptor agonist
The title compounds were synthesised in 7 steps from 1,7-dihydroxynaphthalene as follows: 1,7-dihydroxynaphthalene was methylated and subjected to a Birch reduction to yield 8-methoxy-2-tetralone.


Derivatives of 5-hydroxy-6-methyl-2-aminotetralin.
Three title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation and were potent in a cat cardioaccelerator nerve assay, which involves dopamine receptors.
5,7-Dihydroxy-2-aminotetralin derivatives: synthesis and assessment of dopaminergic and adrenergic actions.
The resorcinol- derived 2-aminotetralins were less potent and less active dopaminergic agents than their catechol-derived isomers, and certain of the subject compounds demonstrated alpha- and beta 1-adrenoceptor activating properties.
N-Alkylated 2-aminotetralins: central dopamine-receptor stimulating activity.
From the biochemical data it is concluded that an n-propyl group on the nitrogen is optimal for activity, and it is suggested that a possible requirement for a potent agonist is that one of it N substituents must fit into a receptor cavity which, because of its size, can maximally accommodate an n -propyl but also smaller groups like ethyl or methyl.
Cerebral dopamine agonist properties of some 2-aminotetralin derivatives after peripheral and intracerebral administration.
Stereotypical behavioral effects produced by direct intracerebral administration of some of the agents were shown to differ strikingly from responses resulting from peripheral administration, and centrally mediated responses of hyperactivity and sterotypical gnawing-biting head and limb movements were showed to be separable in some test compounds.
Selective reactions using metal phenoxides. Part 1. Reactions with formaldehyde
The reactions between formaldehyde and a series of aryloxymagnesium bromides (1) and their complexes with hexamethylphosphoramide (HMPA) in benzene have been investigated. In the absence of ligand
Selective reactions between phenols and formaldehyde. A novel route to salicylaldehydes
Treatment of phenols (1) with 2 mol equiv. of paraformaldehyde in aprotic and poorly electron-donating solvents in the presence of selected metal halides coupled with suitable bases produces