Pyridine → HCID 15907411, compound
Reaction equation
[K+].[CH2:2]([N:9]([CH3:14])[CH2:10][C:11]([O-:13])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:15][CH2:16][CH2:17]O.Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1>ClCCl>[Br:15][CH2:16][CH2:17][O:12][C:11](=[O:13])[CH2:10][N:9]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:14]Participants
Conditions
- Temperature
- 25 °C
Procedure
N-Benzyl-N-methyl glycine potassium salt (2.00 g. 11.16 mmol) and 2-Bromo ethanol (2.48 g. 17.86 mmol) was suspended in 20 mL of dichloromethane. To this solution was added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.40 g. 33.5 mmol) and 4-dimethylamino)pyridine. (1.00 g.) and the reaction was stirred at 25° C. The mixture was diluted with 40 mL of dichloromethane, and was washed with water (1×60 mL), saturated sodium bicarbonate solution (2×60 and brine (1×60 mL). The organic phase was then dried over magnesium sulfate, and filtered through a pad of Celite. Evaporation of the solvent in vacuo affordedd an oil, which was purified on silica gel eluting with ethyl acetate to afford N-Benzyl-N-methyl glycine 2-bromoethyl ester as an oil (0.70 g. 27% yeild).
Workup
- washwas washed with water (1×60 mL), saturated sodium bicarbonate solution (2×60 and brine (1×60 mL)
- dry with materialThe organic phase was then dried over magnesium sulfate
- filtrationfiltered through a pad of Celite
- customEvaporation of the solvent in vacuo affordedd an oil, which
- customwas purified on silica gel eluting with ethyl acetate
Sources & evidence
- ORD record
- ord-9cfe36f2cc294146aa50e0344eb3b118
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291454B1
Reaction notes
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