[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][CH2:7][CH2:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10].[I-].[Na+].O>CN(C)C=O>[N:1]([CH2:6][CH2:7][CH2:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10])=[N+:2]=[N-:3]Sodium azide (2.2 g), 1-(4-chlorobutanoyl)-1,2,3,4-tetrahydroquinoline, prepared in a manner analogous to that set forth in Preparation 1, (4.2 g) and sodium iodide (1.5 g) were heated in dimethylformamide (25 ml) at 90° for 2 hours. The solution was poured into water and extracted with ethyl acetate. The organic solution was washed, dried and evaporated to give 1-(4-azidobutanoyl)-1,2,3,4-tetrahydroquinoline as an oil.
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