[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27].[OH-].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.C(O)C>C(O)C.CC(C)=O>[ClH:27].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1A mixture of 30.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one, 17.8 g of 2-(dimethylamino)ethyl chloride hydrochloride, 13.7 g of 96% potassium hydroxide, 60 g of sodium sulfate and 300 ml of acetone is stirred at 50° C. for 7 hours. After the reaction is completed, the mixture is filtered to remove inorganic materials and the filtrate is condensed. The residue is dissolved in ethanol. After cooling the solution, 10% HCl/ethanol is added thereto. The crystalline precipitates are collected by filtration and then dried. 35.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one hydrochloride are thereby obtained. Yield: 86.2%
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