Water → HCID 12209265, compound

HRID 893890Notes

Reaction equation

HRID 893890 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:12][CH2:13][NH2:14].[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24]Br)[CH3:21].O>CN(C)C=O>[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24][NH:14][CH2:13][CH2:12][C:11]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:9]([O:8][CH3:7])[CH:10]=1)[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8421HomoveratrylamineHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 12209265HCID 12209265, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of anhydrous potassium carbonate (300 g) and 3,4-dimethoxyphenethylamine (148 g, 0.818 m) in dimethylformamide (750 ml) under N2 at 110° C. was added dropwise over 30 min bromoacetaldehyde diethylacetal (167.5 g, 0.850 m). During the addition, the temperature was allowed to rise to 130° C., maintained at 125°-130° C. for 1.5 hours, then the solution cooled. At ca 40° C., 70 ml of water were added, the mixture was stirred for 1 hour, then the inorganic salts were removed by filtration and the solvent evaporated. n-Hexane (750 ml) was added, the precipitated solid was filtered and the filtrate evaporated to an oil, 247 g. This material was vacuum-distilled to give three fractions: (1) b.p. 30°-154° C./0.1 mm, 17.0 g; (2) b.p. 154°-157° C./0.1 mm, 171.6 g; (3) b.p. 157°-174° C./0.1 mm, 37.3 g. Fraction (2) contained the product in 71% yield and 86% purity (GLC).

Workup

  1. additionDuring the addition
  2. customto rise to 130° C.
  3. temperaturemaintained at 125°-130° C. for 1.5 hours
  4. temperaturethe solution cooled
  5. customthe inorganic salts were removed by filtration
  6. customthe solvent evaporated
  7. additionn-Hexane (750 ml) was added
  8. filtrationthe precipitated solid was filtered
  9. customthe filtrate evaporated to an oil, 247 g
  10. distillationThis material was vacuum-distilled
  11. customto give three fractions

Sources & evidence

ORD record
ord-f57182941faa4706bb0c0cec10e998d2
Source dataset
uspto-grants-1981_08
Patent number
US04282146

Reaction notes

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