Acrylamide → HCID 18640066, compound

HRID 1110702Notes

Reaction equation

HRID 1110702 reaction equation
[CH2:1]([N:4]1[C@H:13]2[C@@H:8]([CH2:9][C:10](=O)[CH2:11][CH2:12]2)[CH2:7][CH2:6][C:5]1=O)[CH2:2][CH3:3].[C:16]([NH2:20])(=[O:19])[CH:17]=[CH2:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.COC1C=CC(O)=CC=1>[O:19]=[C:16]1[NH:20][C:10]2[CH2:9][C@H:8]3[C@H:13]([CH2:12][C:11]=2[CH2:18][CH2:17]1)[N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7]3

Participants

6

Reactant 3

HCID 6579AcrylamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 86744078HCID 86744078, compound

Product 1

HCID 18640066HCID 18640066, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (±)-trans-1-propyl-6-oxo-decahydroquinolone (30.0 g, 154 mMol), acrylamide (32.8 g, 462 mMol), p-toluenesulfonic acid monohydrate (35.2 g, 185 mMol), and p-methoxyphenol (500 mg) in toluene (1000 mL) was heated to reflux, water being collected in a Dean-Stark trap. After 17 hr of reflux, the reaction was poured into dilute NaOH solution and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product as a brown foam. Recrystallization (ethyl acetate/hexanes) provided the desired product as a tan solid (14.0 g, 37% yield). Purification of the mother liquors by flash chromatography (2:1 THF: hexanes, 0.5% NH4OH) provided additional product (Rf =0.40, 2.6 g, 7% yield). Recrystallization of this material (ethyl acetate) provided analytically pure material. m.p. =183.0°-184.0°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customwater being collected in a Dean-Stark trap
  4. temperatureAfter 17 hr of reflux
  5. additionthe reaction was poured into dilute NaOH solution
  6. extractionextracted with methylene chloride
  7. dry with materialThe extract was dried (Na2SO4)
  8. concentrationconcentrated
  9. customto give the crude product as a brown foam
  10. customRecrystallization (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-98a4fc35af4e4c2da2d5c2035b1b8dd5
Source dataset
uspto-grants-1990_12
Patent number
US04977149

Reaction notes

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