Morpholine → 3,3-Dimethyl-4-[(morpholinyl)carbonyl]-1,2,3,4-tetrahydroquinoxalin-2-one

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Reaction Steps

To 2.70 g of 4-(chlorocarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one (prepared from 3,3-dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one (EXAMPLE 2) and phosgene) in 30 ml of dichloromethane are added 1.97 g of morpholine. After stirring for 30 min, the reaction mixture is partitioned between dichloromethane and saline. The organic layers are dried over sodium sulfate, concentrated, and crystallized from dichloromethane/hexane to give the title compound, mp 190.5°-193°; MS (m/z) at 289; IR (mineral oil) 1683, 1661, 1409, 1238, 1121, 1506 cm-1 ; NMR (CDCl3) δ 1.3-1.9, 3.0-4.1, 6.70, 6.84, 6.95-7.03, 8.31.

Provenance & Evidence