Potassium Carbonate → HCID 70604238, compound

HRID 1390938Notes

Reaction equation

HRID 1390938 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([CH3:19])[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26]([N:28]([CH2:31][CH2:32][Cl:33])[CH2:29][CH3:30])[CH3:27]>O.CC(C)=O>[ClH:33].[CH2:26]([N:28]([CH2:31][CH2:32][O:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([CH3:19])[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:4][CH:3]=1)[CH2:29][CH3:30])[CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 53812592HCID 53812592, compound

Product 1

HCID 70604238HCID 70604238, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Fifteen grams of the propiophenone derivative are dissolved in 100 ml water-free acetone. Twenty-four grams (200% excess) potash are added while stirring well. Subsequently, 24.0 grams (200% excess) diethylaminoethylchloride, dissolved in 100 ml acetone, are added dropwise. After having boiled it under reflux for 1 day, the precipitate is filtered off, the acetone evaporated and the residue taken up with dry ether. After having precipitated the hydrochloride and sucked off the residue, several recrystallizations from methanol/ether are effected. Ten grams [43.3%] 4-[2-(N,N-diethylamino)-ethoxy]-3,5-dimethyl-β-phenylpropiophenone hydrochloride (melting point of 128° C.) are obtained.

Workup

  1. additionare added dropwise
  2. temperatureunder reflux for 1 day
  3. filtrationthe precipitate is filtered off
  4. customthe acetone evaporated
  5. customAfter having precipitated the hydrochloride
  6. customthe residue, several recrystallizations from methanol/ether

Sources & evidence

ORD record
ord-e73cfc15ca7042719332b73825d294e2
Source dataset
uspto-grants-1979_02
Patent number
US04140770

Reaction notes

Loading…