Potassium Carbonate → 3-[4-(6-Chloro-3-indolyl) piperidin-1-yl]-1-(4-indolyloxy)propane

HRID 977370Notes

Reaction equation

HRID 977370 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]2[CH:8]=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:21][NH:22]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]3[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[CH:9][NH:10]5)[CH2:27][CH2:26]3)=[CH:21][NH:22]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 120720406-Chloro-3-piperidin-4-YL-1H-indole

Product 1

HCID 212683143-[4-(6-Chloro-3-indolyl) piperidin-1-yl]-1-(4-indolyloxy)propane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 99 using 1-chloro-3-(1H-indole-4-oxy)propane (0.446 g, 2.15 mmol) and 6-chloro-3-(piperidin-4-yl)-1H-indole (0.500 g, 2.13 mmol) in the presence of 2.0 equivalents of potassium carbonate (0.593 g, 4.3 mmol) in dimethylformamide at 90° C. Yield 0.330 g (37%) of a colorless foam. FDMS m/e=407 (M+ of free base).

Sources & evidence

ORD record
ord-37f845be66d846fb975bc6db1ab8eff5
Source dataset
uspto-grants-1997_03
Patent number
US05614523

Reaction notes

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