Phenacyl bromide → HCID 68982764, compound

HRID 1821716Notes

Reaction equation

HRID 1821716 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([NH2:11])=[O:10].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O>CC(C)=O>[C:16]1([C:14]2[C:7]([CH2:8][C:9]([NH2:11])=[O:10])=[C:2]3[N:1]([CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 140930093-(Pyridin-2-yl)propanamide

Product 1

HCID 68982764HCID 68982764, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Pyridinepropaneamide (8.0 g, 53 mmol) was dissolved in warm acetone (500 mL). 2-Bromoacetophenone (12.0 g, 60 mmol) was added and the reaction mixture was heated under reflux overnight. After standing at room temperature for 2 days, the solvent was decanted from the tan precipitate, which was dissolved in ethanol and heated under reflux for 6 h. After standing overnight at ambient temperature, the ethanol was removed under reduced pressure to give a residue which was recrystallized from heptane (500 mL) to give 2-(2-phenyl-indolizin-1-yl)acetamide. 2-(2-Phenylindolizin-1-yl)acetamide (450 mg, 1.8 mmol) was suspended in ethyl ether. To the suspension was added lithium aluminum hydride (360 mg) and the reaction mixture was heated under reflux overnight under a nitrogen atmosphere. After cooling to room temperature, an aqueous solution of Rochelle salt was cautiously added with stirring until a solution was observed. The phases were separated and the aqueous phase was extracted 3 times with ether. The combined organic layers were extracted with 0.1 N HCl, and the aqueous layer was made basic with 2.5 N NaOH. The aqueous phase was extracted with methylene chloride three times and the organic phase was evaporated under reduced pressure to give crude product. The product was purified by chromatography on silica gel eluting with 5-11% methanol in methylene chloride containing 1% ammonium hydroxide. A 53% yield of the title compound was obtained, mp 212-214° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solvent was decanted from the tan precipitate, which
  4. dissolutionwas dissolved in ethanol
  5. temperatureheated
  6. temperatureunder reflux for 6 h
  7. waitAfter standing overnight at ambient temperature
  8. customthe ethanol was removed under reduced pressure
  9. customto give a residue which
  10. customwas recrystallized from heptane (500 mL)

Sources & evidence

ORD record
ord-e66179ee9b59477db17f8ffa5bc9c721
Source dataset
uspto-grants-2009_10
Patent number
US07608626B2

Reaction notes

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