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

HRID 1736719Notes

Reaction equation

HRID 1736719 reaction equation
Cl[C:2]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[C:5]1([CH3:16])[CH3:15])=[O:3].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>ClCCl>[CH3:15][C:5]1([CH3:16])[N:4]([C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 229128184-Chlorocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 540550563,3-Dimethyl-4-[(morpholinyl)carbonyl]-1,2,3,4-tetrahydroquinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customthe reaction mixture is partitioned between dichloromethane and saline
  2. dry with materialThe organic layers are dried over sodium sulfate
  3. concentrationconcentrated
  4. customcrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-d411046958e2461894b906f2f2061107
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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