[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12][CH:11]([CH2:16][C:17]([N:19]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=O)[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:19]1([CH2:17][CH2:16][CH:11]2[CH2:12][CH2:13][CH2:14][C:15]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[CH:9][C:10]2=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1A solution of 1-(2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetyl)azepane (60 mg, 0.18 mmol) in anhydrous THF (2 mL) is slowly added to a suspension of LiAlH4 (20 mg, 0.53 mmol) in anhydrous THF (10 mL) cooled to 0° C. The mixture is refluxed for 3 hours following the reaction by means of TLC. The mixture is cooled, and water and a NaOH solution are added, the precipitate is filtered and washed with AcOEt. The organic phase is separated and washed with water and dried, giving 4-(2-(azepan-1-yl)ethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazole (36 mg, 0.11 mmol, 63%, oil).
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