Potassium Carbonate → HCID 66822369, compound

HRID 2406572

Reaction equation

HRID 2406572 reaction equation
Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6]Cl)[CH3:3].[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[CH:15][CH:16]=1)[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 660921-Butanone, 1-(4-hydroxyphenyl)-

Product 1

HCID 66822369HCID 66822369, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Diethylamino)ethyl chloride hydrochloride (624 mg, 3.65 mmol) was added to a stirred solution of p-hydroxybutyrophenone (200 mg, 1.21 mmol) in anhydrous acetone (6 mL) followed by the addition of potassium carbonate (668 mg, 4.84 mmol). The resulting mixture was heated at reflux for 48 hours. The mixture was diluted with ethyl acetate, washed with water (2×) and sat. brine, dried over sodium sulfate, and concentrated to an oil. Flash silica gel column chromatography, eluting with 1:1 hexanes/ethyl acetate, afforded 21 (315 mg, 98%) as a light yellow oil: MS (ES+) m/z 264.1 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 48 hours
  3. washwashed with water (2×) and sat. brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to an oil
  6. washFlash silica gel column chromatography, eluting with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e46f2f20693e44b7b8d6e43fb387b48a
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Linked notes

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