[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][OH:8].[CH2:9]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]([N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6][CH2:7][OH:8])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=16 g of 2-hydroxyethyl-3-hydroxypropylamine and 18,9 g of 1-benzyl-4-piperidone are taken up in 250 ml of methylene chloride and combined at 0° C. with 21.2 g of sodium triacetoxyborohydride. The mixture is stirred over night at ambient temperature, then acidified with 2 N hydrochloric acid and made alkaline with concentrated sodium hydroxide solution. It is extracted with methylene chloride, the extract is dried over sodium sulphate and the solvent is eliminated in vacuo. The residue is chromatographed with ethyl acetate/methanol/conc. ammonia solution 20:80:1 over silica gel. The fractions found to be uniform by TLC are combined and the solvent is eliminated in vacuo. 2.3 g of 1-benzyl-4-[(2-hydroxy-ethyl)-(3-hydroxy-propyl)-amino]-piperidine are obtained as an oil.
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