Phenacyl bromide → HCID 59179408, compound

HRID 2389936Notes

Reaction equation

HRID 2389936 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[C:4]=2[CH2:3][CH2:2]1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>CC(C)=O>[C:21]1([C:19]2[C:10]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])=[C:5]3[N:6]([CH:18]=2)[CH:7]=[CH:8][C:9]2[O:1][CH2:2][CH2:3][C:4]3=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 59179431HCID 59179431, compound

Product 1

HCID 59179408HCID 59179408, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-[3-(2,3-dihydrofuro[3,2-c]pyridin-4-yl)propyl]acetamide (24.5 mg, 0.111 mmol) and 2-bromo-1-phenylethanone (44.2 mg, 0.222 mmol) in acetone (3 mL) was heated under reflux for 13 hr. The reaction mixture was allowed to cool to room temperature and the resulting crystals were collected by filtration and washed with acetone. The crystals were dissolved in ethanol (3 mL), sodium hydrogen carbonate (50 mg) was added, and the mixture was heated under reflux for 1 hr. The reaction mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/50) to give the title compound (12.7 mg, yield 36%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 13 hr
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with acetone
  5. dissolutionThe crystals were dissolved in ethanol (3 mL)
  6. additionsodium hydrogen carbonate (50 mg) was added
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 1 hr
  9. customThe reaction mixture was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/50)

Sources & evidence

ORD record
ord-f68ee830aef14de3a9dc5473cb2fdc28
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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