[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C)C=O.C(O)(C)C.CCOCC>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:15][CH:14]=[CH2:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]A solution of N-acetyl-4-hydroxypiperidine (100 g) in dimethylformamide (250 ml) was added dropwise to sodium hydride (38 g, 50% mineral oil dispersion) under an atomsphere of nitrogen. The mixture was stirred for 2 hours then allyl bromide (93 g) was added slowly while maintaining the reaction temperature at 25° by external cooling. The mixture was then stirred at room temperature overnight, diluted with isopropanol (20 ml) and ether (500 ml), filtered, and evaporated in vacuo. Distillation of the residue gave N-acetyl-4-allyloxypiperidine (108.8 g), b.p. 128°/2 mm, identified spectroscopically.
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