Acetic Acid → 1,3,4,7,8,8a-Hexahydro-3-methyl-6(2H)-isoquinolinone

HRID 1088642Notes

Reaction equation

HRID 1088642 reaction equation
[CH3:1][C:2]([CH:4]=[CH2:5])=O.[C:6]([OH:9])(=O)[CH3:7].[C:10]([O-])(=O)[CH3:11].[Na+].[NH3:15].O1[CH2:21][CH2:20]OCC1>O>[CH3:1][CH:2]1[CH2:4][C:5]2[CH:21]([CH2:10][CH2:11][C:6](=[O:9])[CH:7]=2)[CH2:20][NH:15]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 6570Methyl vinyl ketoneHCID 312751,4-DioxaneHCID 517045Sodium Acetate

Product 1

HCID 221617051,3,4,7,8,8a-Hexahydro-3-methyl-6(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methylvinylketone (24.5 g) was added dropwise to 1-methyl-4-pyrrolidinopiperidin-3-ene (58 g) in dioxane, giving a slight exotherm, keeping the temperature within the range room temperature to 30° C. with cooling. After leaving at room temperature for 45 minutes the solution was refluxed for 3 hours. The mixture was hydrolysed by refluxing for 1 hour with acetic acid (30 mle, sodium acetate (16 g) and water (30 ml). The mixture was poured into ice/water, basified with NH3 (0.880) and extracted 5 times with dichloromethane. The dichloromethane was washed with water (3 times) dried and under vacuum, b.p. 97° C. at 0.8 mm.

Workup

  1. customgiving a slight exotherm
  2. customwithin the range room temperature to 30° C.
  3. temperaturewith cooling
  4. customAfter leaving at room temperature for 45 minutes the solution
  5. temperaturewas refluxed for 3 hours
  6. extractionextracted 5 times with dichloromethane
  7. washThe dichloromethane was washed with water (3 times)
  8. customdried and under vacuum, b.p. 97° C. at 0.8 mm

Sources & evidence

ORD record
ord-89094f03796044c1ac461701dbb2cd45
Source dataset
uspto-grants-1990_10
Patent number
US04963558

Reaction notes

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