[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[C@@H:16]([OH:17])[CH2:15][CH2:14][CH2:13][NH:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C=O.[C:20](O)(=O)C.C(Cl)(Cl)Cl>C(O)C.O=[Pt]=O.CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[C@@H:16]([OH:17])[CH2:15][CH2:14][CH2:13][N:12]2[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
A solution of cis-2-(3,4-dimethoxyphenyl)-3-piperidinol (19.0 g, 80 mmoles, described in Example 4), ethanol (200 ml), 37% aqueous formaldehyde (7.4 g, 91 mmoles) and glacial acetic acid (8.0 g, 131 mmoles) is stirred at room temperature for 2 hours. The solution is diluted to 300 ml with ethanol and hydrogenated in the presence of Adams catalyst (400 mg). The residue is subjected to chromatography on silica gel using chloroform, 5% methanol-chloroform and finally 20% methanol-chloroform. The appropriate eluates are evaporated and the residue is dissolved in acetone. Maleic acid is added, followed by ether. The precipitate is collected and crystallized from acetonitrile-ether to give the title compound as the maleate salt, mp 132°-134° C.
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