Bromoacetyl bromide → 2-bromo-N-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-N-isobutyl-acetamide

HRID 1814737Notes

Reaction equation

HRID 1814737 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11](=[O:18])[CH2:12][NH:13][CH2:14][CH:15]([CH3:17])[CH3:16].[Br:19][CH2:20][C:21](Br)=[O:22]>C1COCC1>[Br:19][CH2:20][C:21]([N:13]([CH2:12][C:11]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:18])[CH2:14][CH:15]([CH3:16])[CH3:17])=[O:22]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 224987871-(3,4-dihydro-1H-isoquinolin-2-yl)-2-isobutylamino-ethanone

Product 1

HCID 224987912-bromo-N-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-N-isobutyl-acetamideYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-(3,4-dihydro-1H-isoquinolin-2-yl)-2-isobutylamino-ethanone (0.45 g, 1.8 mmol) in THF (4.0 mL), a solution of bromoacetyl bromide (0.32 mL, 3.6 mmol) in 4.0 mL THF was added dropwise at −78° C., under argon. After 3 h (the temperature gradually rose to 10° C.) the reaction was concentrated and the remaining residue was diluted with methylene chloride and saturated NaHCO3. The layers were separated and the organic phase was washed with brine and then dried (MgSO4). Filtration and concentration gave the crude product which was purified via silica gel flash chromatography (0-5% MeOH/methylene chloride, 30 mL/min.) to give 0.34 g (51%) of 2-bromo-N-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-N-isobutyl-acetamide.

Workup

  1. concentration) the reaction was concentrated
  2. additionthe remaining residue was diluted with methylene chloride and saturated NaHCO3
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration
  7. customgave the crude product which
  8. customwas purified via silica gel flash chromatography (0-5% MeOH/methylene chloride, 30 mL/min.)

Sources & evidence

ORD record
ord-3e0dd3305ade46019a2f473107d904c6
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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