2-Methoxyethylamine → HCID 45092295, compound
Reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1.57 g of tert-butyl (2-bromoethyl)carbamate (7.0 mmol, 0.7 equivalents) were initially charged in 98.5 ml of acetonitrile, 0.87 ml of 2-methoxyethylamine (750 mg, 10.0 mmol, 1 equivalent) and 3.5 ml of N,N-diisopropylethylamine (2.58 g, 20 mmol, 2 equivalents) were added and the mixture was stirred at 80° C. overnight. The mixture was concentrated and the residue was purified on a silica gel column (mobile phase: dichloromethane/methanol gradient: from 50:1 to 30:1 to 10:1, then dichloromethane/2 N ammonia in methanol: 10:1). This gave 1.69 g (99% of theory; purity about 90%) of the title compound.
Workup
- concentrationThe mixture was concentrated
- customthe residue was purified on a silica gel column (mobile phase
Sources & evidence
- ORD record
- ord-69be9eeae2d34771b7c73e0830dae15c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126998B2
Reaction notes
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