[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]([C:25]#[N:26])([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[OH-].[Na+]>C1COCC1>[CH2:5]([N:12]1[CH2:13][CH2:14][C:15]([C:25]2[NH:26][N:3]=[N:2][N:1]=2)([NH:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:16][CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Sodium azide (5.85 g, 90 mmol) and 1-benzyl-4-cyano-4-anilinopiperidine (2.91 g, 10 mmol) were added slowly to a solution of AlCl3 (2.67 g, 20 mmole) in dry THF (100 ml). The resulting mixture was refluxed overnight. The reaction was quenched with water (50 ml). After separating the THF layer, the aqueous layer was extracted with additional THF (4×50 ml). The combined THF layers were dried over MgSO4 and concentrated in vacuo. The solid obtained was dissolved in 1N.HCl solution and the pH was adjusted to 6.0 with 1N NaOH solution. The resulting mixture was left overnight and filtered to give the product (1.58 g, 4.7 mmol) as white crystalline solid: mp 205°-206° C. (decomposed); IR (nujol) 3300 cm-1 ; NMR (270 MHz, DMSO-d6) δ2.2 to 2.7 (m, 8H, piperidine CH2), 3.53 (s, 2H, benzyl CH2), 6.35, 6.63 and 7.01 (3m, 5H, anilinophenyl H's), 7.25 (m, 5H, benzylphenyl H's). Anal. Calcd. for C19H22N6 : C, 68.24; H, 6.63; N, 25.13. Found: C, 68.79; H, 6.76; N, 24.81. ##STR22##
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