C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)([OH:14])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]A mixture of 5 g of 10% palladized carbon and a solution of 9.8 g of N-benzyl-3-(3,4-dimethoxyphenyl)-3-hydroxy-piperidine [described in French patent No. 2,310,761] in 100 ml of ethanol was placed in an autoclave and hydrogen was introduced to obtain a pressure of 50 kg/cm2. The autoclave was sealed and was heated at 100° C. and the hydrogen pressure stabilized at 65 kg/cm2. The mixture was stirred at 100° C. for 32 hours and was then cooled and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 75-20-5 chloroform-methanol-triethylamine mixture yielded 5.3 g of 3-(3,4-dimethoxyphenyl)-3-hydroxy-piperidine.
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