[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Si]([C:19]#[N:20])(C)(C)C.[Al+3].[Cl-].[Cl-].[Cl-].CS(O)(=O)=O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][C:11]([OH:14])([C:19]#[N:20])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1A solution of N-(3-chloro-2-pyridyl)-4-piperidone (compound 21) (13 g, 62 mmol), TMS-CN (6.2 g, 62 mmol) and AlCl3 (0.1 g) in toluene (100 ml) was heated to 60° C., and stirred overnight. Then 0.1 equivalent of methanesulfonic acid was added, and the reaction mixture was heated to reflux for half an hour. After the reaction was completed, three times of water was added into the reaction solution. The reaction mixture was extracted by ethyl acetate. The organic layer was evaporated to give a crude product, which was purified using column chromatography to give the product. (8 g, 55%)
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