Methyl 4-bromoacetylphenoxyacetate → Methyl 4-[2-[4-(5,6,7,8-tetrahydro-4-quinolinyl)piperazin-1-yl]-acetyl]phenoxyacetate

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Reaction Steps

In a similar manner to Example 1, methyl 4-bromoacetylphenoxyacetate (1.23 g), a 1:1 mixture containing 4-(1-piperazinyl)quinoline and 4-(1-piperazinyl)-5,6,7,8-tetrahydroquinoline (1.84 g) and acetonitrile (56 ml) yielded, after stirring at room temperature overnight, filtration and evaporation of the filtrate, an orange/brown oily residue which was purified by flash chromatography, first on neutral alumina by elution with 5% v/v methanol/dichloromethane, then on silica by elution with methanol/dichloromethane (0.5% v/v to 5% v/v), and finally by crystallisation of the lower Rf material from methanol/water, to yield the title compound (298 mg) as a cream solid: NMR (CDCl3) δ1.76 (2H, m), 1.89 (2H, m), 2.64 (2H, m), 2.76 (4H, m), 2.95 (2H, m), 3.07 (4H, m), 3.80 (2H, s), 3.81 (3H, s), 4.71 (2H, s), 6.68 (1H, d), 6.95 (2H, d), 8.03 (2H, d) 8.28 (1H, d); m/Z 424 (M+H)+ ; calculated for C24H29N3O4. 1.0 H2O: C, 65.3%; H, 7.08%; N, 9.52%; found: C, 65.6%; H, 6.7%; N, 9.3%.

Provenance & Evidence