Synthesis of Bishomobenzoctamine 2-(9,10-Dihydro-9,10-Propanoanthracen-9-yl)-N-Methylethanamine

Abstract

Tetracyclic bishomobenzoctamine as a homologue of benzoctamine 1 was synthesised. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one was successfully synthesised via [3+4] cycloaddition of tetrabromoacetone on 9-allylanthracene by using ultrasonication at 15-20 °C followed by debromination.

11-Hydroxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one

“…For background to benzoctamine, see: Wilhelm & Schmidt (1969); Karama et al (2010a). For further synthetic details, see: Karama et al (2010b). For ring conformations, see: Cremer & Pople (1975).…”

“…Benzoctamine is a clinically useful drug for the treatment of anxiety (Wilhelm & Schmidt, 1969) and our research group recently reported (Karama et al, 2010a) the synthesis of bishomobenzoctamine (Karama et al, 2010b) as it is a structural mimic of benzoctamine and was derived from anthrone which might be exhibited antidepressant activity. The title compound is the key intermediate for the synthesis of bishomobenzoctamine and its crystal structure is presented here.…”

Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition

“…Studies on the structure-activity relationship (SAR) of this molecules led us recently [2] to synthesize the corresponding bishomobenzoctamine, 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)- N -methylethanamine ( 2, Figure 1)via a [3+4] cycloaddition at 15–20 ºC [3]. …”