Morpholine → 4-(7-Bromoquinoxalin-2-yl)morpholine

HRID 929345Notes

Reaction equation

HRID 929345 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](Cl)=[N:9]2)=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 49132537-Bromo-2-chloroquinoxaline

Product 1

HCID 533635264-(7-Bromoquinoxalin-2-yl)morpholineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 7-bromo-2-chloroquinoxaline (50 g, 0.2 mol, 1.0 eq.) in CH3CN (200 mL) were added morpholine (89 g, 1.02 mol, 5.0 eq.) and K2CO3 (85 g, 0.61 mol, 3.0 eq). The resulting mixture was stirred at 90° C. for 2 h, then cooled and filtered. The filtrate was concentrated and the residue was re-crystallized from EA to afford 4-(7-bromoquinoxalin-2-yl)morpholine (59 g, 98.3%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was re-crystallized from EA

Sources & evidence

ORD record
ord-cc35c464d80e44ea96b8887d47543faf
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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