4-Chloro-1,2-diaminobenzene → 5-(5-Chlorobenzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278023

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]2[N:26]=[C:1]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][CH:11]=3)[NH:8][CH:7]=[C:6]4[CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[NH:27][C:22]=2[CH:21]=1

Participants

Conditions

Temperature: 155 °C

Procedure

A solution of 5-formyl-3-(1-methylpiperidin-4-yl)-1H-indole (0.210 g, 0.90 mmol), and 4-chloro-o-phenylenediamine (0.197 g, 1.38 mmol), in 15 mL of nitrobenzene was heated, with stirring, at 150-160° C. for 24 hours. The solution was allowed to cool to room temperature, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography (dichloromethane:methanol 10:1.5) to give the title compound (0.215 g, 68%) as an amorphous tan solid. FDMS m/e=365 (M+). EA calculated for C21H21N4Cl.¼ H2O C, 68.28; H, 5.87; N, 15.17. Found: C, 68.32; H, 6.17; N, 14.51.

Workup

temperatureto cool to room temperature
customthe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography (dichloromethane:methanol 10:1.5)

Sources & evidence

ORD record: ord-36ac999f03b647a684a4681048bee2a7
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358972B1

Linked notes

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