Dimethylamine → 1-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:22][NH:23][CH3:24]>>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:23]([CH3:24])[CH3:22])=[CH:16][CH:15]=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]Participants
3
Procedure
30 ml of 40% aqueous dimethylamine solution was added to 4.5 g (14.5 mmol) of 1-[[[4-(chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester, and the mixture was heated under reflux for 3 hours. The reaction mixture was distilled off under reduced pressure, a saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, diisopropyl ether was added to the residue, and the mixture was stirred overnight. The precipitated solid was collected by filtration to obtain 2.3 g (50%) of the title compound.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 3 hours
- distillationThe reaction mixture was distilled off under reduced pressure
- additiona saturated aqueous sodium bicarbonate solution was added
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried with anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure, diisopropyl ether
- additionwas added to the residue
- filtrationThe precipitated solid was collected by filtration
Sources & evidence
- ORD record
- ord-0344ca7c4c3b4756b0f2a7342ba25da8
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829209B2
Reaction notes
Loading…