Morpholine → 4-(6-Bromoquinolin-4-yl)morpholine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 6-bromo-4-chloro-quinoline (1.0 g, 4.12 mmol) and morpholine (9.98 g, 114.6 mmol) was heated to 150° C. in a sealed tube and stirred for 2 days. Then, the brown suspension was diluted with water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to afford 1.06 g (87.7% yield) of 6-bromo-4-morpholin-4-yl-quinoline as a light brown solid: EI-LRMS m/e calcd for C13H13BrN2O (M+) 293.1, found 293.1.
Workup
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined extracts were washed with brine solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtration of the drying agent
- customthe filtrate was removed under the vacuum
- customthe residue was purified
Sources & evidence
- ORD record
- ord-bbe1315103df41668b4e4bae734f5288
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253285B2
Reaction notes
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