3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → HCID 10179122, compound

HRID 1766256Notes

Reaction equation

HRID 1766256 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([OH:29])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1.[OH-].[Na+]>>[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:29][S:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)(=[O:11])=[O:10])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 10179122HCID 10179122, compoundYield 49%

Procedure

By a method similar to Example 31, using 4-methoxybenzenesulfonyl chloride (248 mg, 1.2 mmol) and 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (230 mg, 1.0 mmol), 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) gave 225 mg of crude product. The crude product was recrystallized from ethyl acetate to give 195 mg (49%) of the title compound as a white powder: mp=186-187° C.; MS(m/e): 400 (M+); Calculated for C21H24N2O4S: Calcd: C, 62.98; H, 6.04; N, 6.99. Found: C, 63.10; H, 6.18; N, 7.04.

Workup

  1. customgave 225 mg of crude product
  2. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6122a477796e4553a6bd3d374a736110
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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