S(=O)(=O)(O)O.[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:12][CH2:13][OH:14].[OH-].[Ba+2].[OH-].C(=O)=[O:19]>O.[O-2].[O-2].[O-2].[Cr+6]>[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:12][C:13]([OH:19])=[O:14]A solution of chromium trioxide (20 g, 200 mmol) in water (300 ml) and concentrated sulfuric acid (40 g, 73.6 ml) was added dropwise in the course of 1.5 h, while cooling with ice, to a solution of 2-piperidineethanol (10.0 g, 10.1 ml, 77.4 mmol) in water (10 ml). The reaction mixture was stirred for 3 h at room temperature. The solution was then rendered alkaline with saturated aqueous barium hydroxide solution. Carbon dioxide was then passed into the solution, and the resulting suspension was filtered through Celite. The filtrate was concentrated in vacuo.
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