2-(Dimethylamino)ethanol → 6-(2-Dimethylaminoethoxy)-1-tetralone

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Reaction Steps

Ether linked analogs such as 61, are prepared by the convergent synthesis depicted in scheme 15. The 6-hydroxy-1-tetralone 15 is reacted with an amine, such as N,N-dimethylethanolamine, preferably in the presence of PPh3 and DEAD at a temperature preferably between about 0° C. and about RT to form the 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 59. The 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 59 is reacted with hydroxylamine hydrochloride and base, such as Et3N. The reaction is heated above RT, preferably at reflux to form the oxime 60. Hydrogenation of the oxime 60, such as with Pd/C and H2 provides the amine 61.

Provenance & Evidence