Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(N(CC)CC)C.Cl[C:19]([C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:20]>ClCCl>[CH3:1][N:2]([CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[C:19]([C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:20]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
Into a 100-mL round-bottom flask, was placed a solution of N-methyl-2-morpholinoethanamine (2.1 g, 13.12 mmol, 1.00 equiv, 90%) in dichloromethane (20 mL), and triethylamine (1.47 g, 14.55 mmol, 1.00 equiv). This was followed by the addition of a solution of methyl 3-(chlorocarbonyl)benzoate (3.3 g, 15.00 mmol, 1.20 equiv, 90%) in dichloromethane (10 mL) dropwise with stirring at 0-5° C. The resulting solution was stirred for 3 h at room temperature. The resulting solution was diluted with 100 mL of dichloromethane. The resulting mixture was washed with 1×30 mL of 10% sodium bicarbonate. The resulting mixture was washed with 1×30 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane:methanol (20:1). This resulted in 4.4 g (99%) of methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate as a brown solid.
Workup
- customInto a 100-mL round-bottom flask, was placed
- stirringThe resulting solution was stirred for 3 h at room temperature
- washThe resulting mixture was washed with 1×30 mL of 10% sodium bicarbonate
- washThe resulting mixture was washed with 1×30 mL of brine
- dry with materialThe mixture was dried over sodium sulfate
- concentrationconcentrated under vacuum
- customThis resulted in 4.4 g (99%) of methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate as a brown solid
Sources & evidence
- ORD record
- ord-cfe97405300d4a2a85f5d5ccf8662c63
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Linked notes
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