Bromoacetyl bromide → HCID 22498793, compound
Reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][NH:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].[Br:16][CH2:17][C:18](Br)=[O:19]>C1COCC1>[Br:16][CH2:17][C:18]([N:4]([CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of the above 2-(2,2-dimethyl-propylamino)-1-morpholin-4-yl-ethanone (0.18 g, 0.8 mmol) in THF (2.0 mL), a solution of bromoacetyl bromide (0.15 mL, 1.6mmol) in THF (2.0 mL) was added, dropwise at −78° C., under nitrogen. After 3 h the reaction was concentrated and the resulting residue was diluted with methylene chloride and saturated NaHCO3. The layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried (MgSO4), filtered and concentrated to give the crude product. Purification via silica gel flash chromatography, eluting with EtOAc, flow rate 30 mL/min, gave 0.10 g (36%) of 2-bromo-N-(2,2-dimethyl-propyl)-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamide.