Sodium Hydroxide → Ketoamine 1-diethylamino-6-m-methoxyphenylhexan-3-one

HRID 1414944Notes

Reaction equation

HRID 1414944 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH3:2].[OH-:20].[Na+]>S(=O)(=O)(O)O.O>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6](=[O:20])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH3:19].[O:20]=[NH:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 214855971-Diethylamino-6-m-methoxyphenylhex-2-yne

Product 1

HCID 86733483Ketoamine 1-diethylamino-6-m-methoxyphenylhexan-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Add mercuric sulphate (0.45 g) to a swirled solution of 1-diethylamino-6-m-methoxyphenylhex-2-yne (8.5 g) in concentrated sulphuric acid (2.5 cc) and water (25 cc). Keep the solution under nitrogen at 75° C for 1 hour, then cool, make basic with 10% aqueous sodium hydroxide, and filter through glass wool to remove mercuric oxide. Extract product with ether and wash and dry the ethereal solution. Remove the solvent to obtain the crude ketoamine 1-diethylamino-6-m-methoxyphenylhexan-3-one, infrared absorption peak at 1710 μ. Distil under reduced pressure with partial elimination of diethylamine, to obtain a mixture of the ketoamine 1-diethylamino-6-m-methoxyphenylhexan-3-one and the vinyl ketone 6-m-methoxyphenylhex-1-en-3-one (7.1 g, ca. 76%), b.p. 140°-145° C/0.1 mm; infrared absorption peaks at 5.85 and 5.95 μ, the ketoamine predominating.

Workup

  1. customat 75° C
  2. customfor 1 hour
  3. temperaturecool
  4. filtrationfilter through glass wool
  5. customto remove mercuric oxide
  6. washExtract product with ether and wash
  7. customdry the ethereal solution
  8. customRemove the solvent

Sources & evidence

ORD record
ord-3601d772f98d4e82a0377522e641b341
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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