[Mg].Br[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Cl:13])=[CH:5][CH:4]=1.[N:14]1[CH:19]=[CH:18][C:17]([C:20]#N)=[CH:16][CH:15]=1.[Cl-].[NH4+].[H][H].CC[O:28]CC>C(Br)C.C1C=CC=CC=1.[Rh]>[ClH:13].[Cl:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH:20]([CH:17]2[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]2)[OH:28])=[CH:4][CH:5]=1To a flask containing 1.8 g (72 mmoles) of magnesium turnings and 20 ml of anhydrous ether under nitrogen is added 10 drops of ethyl bromide. The ether is heated to reflux and a solution of 10 g (50 mmoles) of 1-bromo-4-chloronaphthalene in 150 ml of dry ether added gradually during 30 minutes and refluxing continued for 8 hours. 60 g (58 mmoles) of 4-pyridinecarbonitrile in 100 ml of benzene is added gradually and the solution refluxed for 3 hours and the adduct decomposed by addition of saturated ammonium chloride solution. The resulting 4-(4-chloro-1-naphthoyl)pyridine is extracted into ether and the organic phase washed with brine and dried over magnesium sulfate. The ether is removed in vacuo and the residue dissolved in methanol and reduced by reaction with 200 mmoles of hydrogen gas in the presence of a rhodium catalyst. The catalyst is filtered off, an excess of alcoholic hydrochloride acid is added, and the solution concentrated in vacuo. The residue is recrystallized from isopropanol to yield α-(4-chloro-1-naphthyl)-4-piperidinemethanol hydrochloride.
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