Potassium Sodium Tartrate → HCID 11557725, compound

HRID 1821717Notes

Reaction equation

HRID 1821717 reaction equation
[C:1]1([C:7]2[C:8]([CH2:16][C:17]([NH2:19])=O)=[C:9]3[N:14]([CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C>[C:1]1([C:7]2[C:8]([CH2:16][CH2:17][NH2:19])=[C:9]3[N:14]([CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68982764HCID 68982764, compound

Product 1

HCID 11557725HCID 11557725, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 under a nitrogen atmosphere
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted 3 times with ether
  5. extractionThe combined organic layers were extracted with 0.1 N HCl
  6. extractionThe aqueous phase was extracted with methylene chloride three times
  7. customthe organic phase was evaporated under reduced pressure
  8. customto give crude product
  9. customThe product was purified by chromatography on silica gel eluting with 5-11% methanol in methylene chloride containing 1% ammonium hydroxide

Sources & evidence

ORD record
ord-a3116cf90a73458b8e83fb74e42ab240
Source dataset
uspto-grants-2009_10
Patent number
US07608626B2

Reaction notes

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