Potassium Carbonate → (1H-benzimidazol-2-yl)-[1-(6-methoxy-1-methyl-1H-indol-3-ylmethyl)-piperidin-4-ylmethyl]-amine

HRID 2109991Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[I-].[CH3:19][O:20][C:21]1[CH:29]=[C:28]2[C:24]([C:25]([CH2:31][N+](C)(C)C)=[CH:26][N:27]2[CH3:30])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:31][C:25]2[C:24]3[C:28](=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[N:27]([CH3:30])[CH:26]=2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 50 °C

Procedure

After adding anhydrous acetonitrile (2 ml) to a mixture of (1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine (20 mg, 0.09 mmol), (6-methoxy-1-methyl-1H-indol-3-ylmethyl)-trimethylammonium iodide (0.1 mmol) and anhydrous potassium carbonate (5 mg, 0.11 mmol), the mixture was stirred at 50° C. for 12 hours. The mixture was cooled to room temperature and then passed through a silica gel short column and purified by preparative HPLC to obtain (1H-benzimidazol-2-yl)-[1-(6-methoxy-1-methyl-1H-indol-3-ylmethyl)-piperidin-4-ylmethyl]-amine. The compound was identified by LC-MS.

Workup

temperatureThe mixture was cooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-590ac5c36352422c89a3212712c12b12
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517875B2

Reaction notes

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