Sodium Hydroxide → 1-Diethylamino-6-(3,4-dimethoxyphenyl)hexan-3-one

HRID 1414947Notes

Reaction equation

HRID 1414947 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH3:2].[OH-:22].[Na+]>S(=O)(=O)(O)O.O>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6](=[O:22])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 214857251-Diethylamino-6-(3,4-dimethoxyphenyl)hex-2-yne

Product 1

HCID 214854151-Diethylamino-6-(3,4-dimethoxyphenyl)hexan-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Add mercuric sulphate (0.45 g) to a stirred solution of 1-diethylamino-6-(3,4-dimethoxyphenyl)hex-2-yne (8.5 g) in concentrated sulphuric acid (2.5 cc) and water (25 cc) and maintain the solution at 75° for 90 minutes. Make the cooled solution basic with 10% aqueous sodium hydroxide and filter to remove mercuric oxide. Extract the product with ether and wash and dry the ethereal solution. Evaporate the solvent to obtain 1-diethylamino-6-(3,4-dimethoxyphenyl)hexan-3-one as an oily residue.

Workup

  1. temperaturemaintain the solution at 75° for 90 minutes
  2. filtrationfilter
  3. customto remove mercuric oxide
  4. extractionExtract the product with ether
  5. washwash
  6. customdry the ethereal solution
  7. customEvaporate the solvent

Sources & evidence

ORD record
ord-1556663cc20840f5971932548e534090
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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