1,4-Dioxa-8-azaspiro(4.5)decane → (3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidone ethylene ketal
Reaction equation
[CH3:1][C:2]1[N:6]=[C:5](C(Cl)(Cl)Cl)[O:4][N:3]=1.[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH2:12]1>C(O)C>[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][N:17]([C:5]3[O:4][N:3]=[C:2]([CH3:1])[N:6]=3)[CH2:16][CH2:15]2)[O:13][CH2:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Methyl-5-trichloromethyl-1,2,4-oxadiazole (Moussebois and Eloy, Helv. Chim. Acta 1964, 47, 838) (1 g, 5 mmol) and 4-piperidone ethylene ketal (1.5 g, 10 mmol) in ethanol (20 ml) were heated reflux overnight. The solvent was evaporated and the residue taken up in dichloromethane and filtered. The filtrate was washed with dilute HCl, dried over sodium sulphate and evaporated to leave a pale yellow oil (0.22 g). The acid washing was neutralised with solid sodium bicarbonate and extracted with dichloromethane. Evaporation gave further oil (0.17 g, total 0.39 g), MS (+EI) 225 (M+).