3-Phenylpropanamide → 4-(2,2-dimethyl-1-oxopropyl)-N-(3-phenylpropionyl)-benzamide

HRID 1768675Notes

Reaction equation

HRID 1768675 reaction equation
[H-].[K+].[C:3]1([CH2:9][CH2:10][C:11]([NH2:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[C:15]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:13][C:11](=[O:12])[CH2:10][CH2:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:26])=[CH:23][CH:22]=1)=[O:20]

Participants

6

Reactant 4

HCID 76253-PhenylpropanamideHCID 82127Potassium hydrideHCID 166653HydrideHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-

Product 1

HCID 152328444-(2,2-dimethyl-1-oxopropyl)-N-(3-phenylpropionyl)-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A slurry of potassium hydride (from 46 grams of 35% potassium hydride in oil washed three times with hexane)in 50 ml of THF is added with stirring under nitrogen to 20 grams of 3-phenylpropionamide in 350ml of THF. After addition of the hydride is complete, the reaction is allowed to warm to room temperature and is stirred for 30 minutes. The thickened reaction mixture is cooled to 0° to 5° C. and is then added dropwise over 30 minutes to a solution of 30 grams of p-pivaloylbenzoyl chloride in 50 ml of dry THF. The resulting solution is stirred for 15 minutes at 0° to 5° C. and is then quenched with 150 ml of saturated ammonium chloride solution. The THF phase is decanted off, and the aqueous phase is extracted with ethyl acetate. The ethyl acetate extract is combined with the THF phase, dried with magnesium sulfate, filtered, and then evaporated almost to dryness. The resulting solids are triturated with ether, and the white crystals obtained are filtered, washed with ether and dried to yield the title product (m.p. 137°-138° C.).

Workup

  1. customThe thickened reaction mixture
  2. temperatureis cooled to 0° to 5° C.
  3. stirringThe resulting solution is stirred for 15 minutes at 0° to 5° C.
  4. customis then quenched with 150 ml of saturated ammonium chloride solution
  5. customThe THF phase is decanted off
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. customevaporated almost to dryness
  11. customThe resulting solids are triturated with ether
  12. customthe white crystals obtained
  13. filtrationare filtered
  14. washwashed with ether
  15. customdried

Sources & evidence

ORD record
ord-84a297d3c16e42ddafa1ef646cebfca4
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

Loading…