Bromoacetyl bromide → 2-bromo-N-isobutyl-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamide

HRID 1814734Notes

Reaction equation

HRID 1814734 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])[CH:2]([CH3:4])[CH3:3].[Br:15][CH2:16][C:17](Br)=[O:18]>C1COCC1>[Br:15][CH2:16][C:17]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])=[O:18]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 224987892-Isobutylamino-1-morpholin-4-yl-ethanone

Product 1

HCID 224987902-bromo-N-isobutyl-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Isobutylamino-1 -morpholin-4-yl-ethanone (1.43 g, 7.13 mmol) was dissolved in 15 mL of THF. To this solution at −78° C. was added a solution of bromoacetyl bromide (1.24 mL, 14.3 mmol) in 15 mL of THF. The mixture was warmed to room temperature and stirred for 2 h. Solvent was removed in vacuo. The residue was dissolved in 30 mL of methylene chloride, washed with saturated sodium bicarbonate, and brine, then dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by silica gel flash chromatography eluting with 2% MeOH in methylene chloride to give 2-bromo-N-isobutyl-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamide (1.37 g, 60%) as a clear oil.

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 30 mL of methylene chloride
  3. washwashed with saturated sodium bicarbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel flash chromatography
  7. washeluting with 2% MeOH in methylene chloride

Sources & evidence

ORD record
ord-e259e712a1a64e3abde149031bad3697
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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