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

Participants

Reaction Steps

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.

Provenance & Evidence