Dichloromethane → Ethyl 2-(benzylamino)acetate Hydrochloride
Reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(Cl)[Cl:24]>>[ClH:24].[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:22]Participants
Procedure
In a 3 liter erlenmeyer flask was placed 107.2 g (1.0 mole) of benzylamine, 152.0 g (1.5 mole) of triethylamine and 1.5 liter of methylene chloride. The resulting solution was stirred while 167.0 g (1.0 mole) of ethyl bromoacetate was added dropwise. The mixture was washed with water (3×300 mL), dried over magnesium sulfate, filtered and solvent was removed by rotary evaporation. The resulting oil was dissolved in ether and hydrogen chloride saturated ether was then added slowly until precipitation was complete. The precipitate was a gummy solid and the mixture was stoppered and let sit for one day. Over this time the precipitate formed a hard solid which was filtered off and dried in vacuum to give 62.8 g (28%) of N-benzylglycine ethyl ester hydrochloride.
Workup
- customIn a 3 liter erlenmeyer flask was placed
- additionwas added dropwise
- washThe mixture was washed with water (3×300 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customsolvent was removed by rotary evaporation
- dissolutionThe resulting oil was dissolved in ether
- additionhydrogen chloride saturated ether was then added slowly until precipitation
- customOver this time the precipitate formed a hard solid which
- filtrationwas filtered off
- customdried in vacuum
Sources & evidence
- ORD record
- ord-2dc907d7d0c74193b27e18ef73470e44
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05221665
Reaction notes
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