[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
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.
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