[Mg].II.Br[C:5]1[CH:6]=[C:7]([O:11][CH3:12])[CH:8]=[CH:9][CH:10]=1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-:27].[NH4+]>CCOCC.O1CCCC1>[ClH:27].[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:22]2([OH:26])[CH2:23][CH2:24][CH2:25][N:20]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:21]2)[CH:10]=[CH:9][CH:8]=1
9 g of magnesium were activated by sublimation of iodine and were cooled and 20 ml of ether and 2 ml of tetrahydrofuran were added thereto. Then, 2 ml of m-bromoanisole were added thereto under an inert atmosphere and the reaction began. Then, a solution of 50 ml of m-bromoanisole in 200 ml of ether and 20 ml of tetrahydrofuran were added dropwise to the mixture over 2 hours and the mixture was refluxed for one hour and allowed to stand for 16 hours. 120 ml of the solution were cooled to 5° to 10° C. while adding a solution of 20 g of N-benzyl-3-piperidone in 100 ml of tetrahydrofuran dropwise under an inert atmosphere. The mixture was stirred for 3 hours and was then cooled in an ice bath. 200 ml of aqueous saturated ammonium chloride solution were added dropwise to the mixture at 5° to 20° C. and the mixture was vacuum filtered. The decanted aqueous phase was extracted with ethyl acetate and the ethyl acetate extract was extracted with 2 N hydrochloric acid. The aqueous extract was made alkaline by addition of sodium hydroxide and was extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The 30 g of residue were dissolved in ethyl acetate and a solution of hydrogen chloride gas in ethyl acetate was added thereto until the pH was acidic. Crystallization was induced and the mixture was vacuum filtered to obtain 3-(3-methoxyphenyl)-1-benzyl-piperidine-3-ol hydrochloride melting at 210° C.
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