N-Methyl-2,2'-diaminodiethylamine → tert-Butyl {2-[(2-aminoethyl)(methyl)amino]ethyl}carbamate
Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH3:8])[CH2:5][CH2:6][NH2:7].[C:9]([O:13][C:14](=O)[O:15]C(C)(C)C)([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][N:4]([CH3:8])[CH2:5][CH2:6][NH:7][C:14](=[O:15])[O:13][C:9]([CH3:12])([CH3:11])[CH3:10]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
N1-(2-Aminoethyl)-N1-methylethane-1,2-diamine (5.0 g, 42.7 mmol) was dissolved in 100 mL of CH2Cl2 and cooled to 0° C. A solution of di-tert-butylcarbonate (0.93 g, 4.27 mmol) in CH2Cl2 (10 mL) was then added dropwise at 0° C. over a period of 15 min. The resulting reaction mixture was stirred at 0° C. for 30 min and then warmed to room temperature. After stirring at room temperature for 2 h, the reaction mixture was diluted with CH2Cl2 (100 mL). The organic layer was washed with brine (3×25 mL), dried (Na2SO4) and concentrated under reduced pressure to afford 1.1 g of tert-butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate.
Workup
- customThe resulting reaction mixture
- temperaturewarmed to room temperature
- stirringAfter stirring at room temperature for 2 h
- washThe organic layer was washed with brine (3×25 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0c13a812703842e48a896f580d5dab4e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969354B2
Reaction notes
Loading…