[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH2:17][CH2:16]2)[C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.Cl.[O:28]1CCOCC1>[OH-].[Na+].O=O.[Pt]>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][O:23][CH2:24][C:25]([OH:28])=[O:26])[CH2:19][CH2:20]2)=[CH:13][CH:12]=1To a stirred and heated (80° C.) suspension of hydroxyzine hydrochloride (1.0 g, 2.23 mmol) and 5% Pt/C in dioxane (10 mL) and 1N aqueous NaOH solution (10 mL), O2 was bubbled through for 20 hours. After being cooled down to room temperature, The mixture was filtered through a pad of celite (2.5×2 cm) and washed with water. The filtrate was extracted with dichloromethane (3×25 mL). The combined organic solution was dried (Na2SO4). Evaporation of solvent gave the titled compound as a pale white form (0.51 g, yield 58.7%).
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