[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[CH2:2].[O-]Cl.[Na+].[N:12]1([CH2:18][CH2:19][CH:20]=[N:21][OH:22])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[N:12]1([CH2:18][CH2:19][C:20]2[CH2:2][CH:1]([N:3]3[CH2:7][CH2:6][CH2:5][C:4]3=[O:8])[O:22][N:21]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1To a solution of 646 μL (1.5 equivalent) of N-vinyl-pyrrolidin-2-one in 5 mL of chloroform, a biphasic solution of 7.4 mL (3.2 equivalents) of 13% Clorax (NaOCl) and a solution of 629.3 mg (4.03 mmol) of 3-piperidin-1-yl-propionaldehyde oxime compound prepared in Example 2 in 5 mL of chloroform were added slowly over 15 minutes with cooling to 0° C. and stirring vigorously. After reacting at room temperature overnight, the reaction mixture was extracted with chloroform three times, washed with a saturated aqueous solution of sodium carbonate twice following water once, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The concentrate was purified by separation with silica gel column chromatography using chloroform/methanol (30:1) as eluent to obtain 477.4 mg (45% yield) of 1-[3-(2-piperidin-1-yl-ethyl)-4,5-dihydro-isoxazol-5-yl]-pyrrolidin-2-one. Subsequently, 1:1 acid addition salt with oxalic acid was obtained from the diethyl ether solution.
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