Acrylamide → HCID 18640066, compound

HRID 2165265Notes

Reaction equation

HRID 2165265 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 The extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated
  9. customto give the crude product as a brown foam
  10. customRecrystallization (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a49da64e58c741ea8ac304700c5cda5f
Source dataset
uspto-grants-1990_07
Patent number
US04939259

Reaction notes

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