C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[C:12]([C:15]1[CH:27]=[CH:26][C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=1)(=[O:14])[CH3:13].[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=1.C(=O)=O.Cl>CO>[NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]1[CH2:13][C:12]([C:15]1[CH:27]=[CH:26][C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=1)=[O:14]Magnesium methyl carbonate (0.6 mole, 2.5 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 2-acetyldibenzofuran, 31.5 g (0.15 mole) is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen to form the chelate, allowing the methyl alcohol that forms to escape. The mixture is cooled to room temperature under an atmosphere of carbon dioxide and 15.2 g (0.18 mole) of 2,3,4,5-tetrahydropyridine (as α-tripiperidine) is added and the mixture stirred at room temperature for a period of 40 hours in an atmosphere of carbon dioxide. The resulting mixture is poured into 200 ml of concentrated HCl on 600 g of ice. After standing for 48 hours the precipitate which forms is filtered and washed with ethyl ether. The 2-dibenzofuranyl-2-piperidylmethyl ketone so prepared is twice recrystallized from isopropyl alcohol as the hydrochloride salt and is obtained in 32% yield (16.0 g) and has a M.P. of 218-20°C. (dec.)
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