Bromoacetyl bromide → HCID 22498793, compound

HRID 1814742Notes

Reaction equation

HRID 1814742 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

HCID 61147Bromoacetyl bromideHCID 22498786HCID 22498786, compound

Product 1

HCID 22498793HCID 22498793, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. concentrationAfter 3 h the reaction was concentrated
  2. additionthe resulting residue was diluted with methylene chloride and saturated NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with methylene chloride
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customPurification via silica gel flash chromatography
  10. washeluting with EtOAc, flow rate 30 mL/min

Sources & evidence

ORD record
ord-aabbb1a2e9a64901af9c71489917fa77
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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