N-Methylbenzeneethanamine → N-methyl-N-phenethyl-2-bromoacetamide
Reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:6][N:7]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3](=[O:4])[CH2:2][Br:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -25 °C
Procedure
To a solution of 27.07 g (171.95 mmol) of bromoacetyl chloride in 100 ml of methylene chloride, cooled to -25° C. by means of an external cooling bath, is added dropwise a solution of 46.5 g (343.9 mmol) of N-methyl-N-phenethyl amine in 50 ml of methylene chloride over a period of 11/2 hours. The reaction mixture is stirred at -25° C. for additional 15 minutes and then allowed to equilibrate to room temperature. The reaction mixture is then partitioned between methylene chloride and water. The organic layer is washed with 1N aqueous HCl solution and water, dried over magnesium sulfate and concentrated in vacuo to give N-methyl-N-phenethyl-2-bromoacetamide which is used directly in the next step.
Workup
- customto equilibrate to room temperature
- customThe reaction mixture is then partitioned between methylene chloride and water
- washThe organic layer is washed with 1N aqueous HCl solution and water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-51a646d0e6b44ea480daff1cf989f545
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05468898
Reaction notes
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