Water → N-(2-Oxo-1-phenylpropyl)hexanamide

HRID 1982436Notes

Reaction equation

HRID 1982436 reaction equation
Cl.[NH2:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](=[O:6])[CH3:5].O.C(=O)([O-])[O-].[K+].[K+].[C:20](Cl)(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(OCC)(=O)C>[C:20]([NH:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](=[O:6])[CH3:5])(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67340Hexanoyl chlorideHCID 27970031-amino-1-phenylpropan-2-one hydrochloride

Product 1

HCID 13293301N-(2-Oxo-1-phenylpropyl)hexanamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-amino-1-phenyl-2-propanone hydrochloride (5.55 g), water (40 ml), ethyl acetate (75 ml) and potassium carbonate (4.55 g) was added dropwise hexanoyl chloride (4.42 g) under ice-cooling and stirring. The mixture was further stirred for an hour with ice-cooling. The ethyl acetate layer was separated, washed with water, diluted hydrochloric acid and water in that order, and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was recrystallized from isopropyl ether to give crystals of 1-hexanoylamino-1-phenyl-2-propanone, yield 5.80 g (78.2%), m.p. 77°-78° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was further stirred for an hour with ice-
  3. temperaturecooling
  4. customThe ethyl acetate layer was separated
  5. washwashed with water, diluted hydrochloric acid and water in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off
  8. customthe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-839689b51daf449195babcbe1f0eb571
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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