Triethylamine → Methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate

Temperatur

2.5 °C

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.

1. customInto a 100-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 3 h at room temperature
3. washThe resulting mixture was washed with 1×30 mL of 10% sodium bicarbonate
4. washThe resulting mixture was washed with 1×30 mL of brine
5. dry with materialThe mixture was dried over sodium sulfate
6. concentrationconcentrated under vacuum
7. customThis resulted in 4.4 g (99%) of methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate as a brown solid

ORD-Eintrag

ord-cfe97405300d4a2a85f5d5ccf8662c63

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09301951B2