3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → HCID 10201262, compound

HRID 1766255Notes

Reaction equation

HRID 1766255 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([OH:28])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][S:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)(=[O:10])=[O:9])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 10201262HCID 10201262, compoundYield 97.8%

Procedure

By a method similar to Example 31, using 4-chlorobenzenesulfonyl chloride (242 mg, 1.15 mmol) and 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (220 mg, 0.96 mmol), 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) gave 380 mg of a white solid. The crude product was recrystallized from ethyl acetate/hexanes to give 300 mg (78%) of the title compound as an off white powder: mp=182-183.5° C.; MS(m/e): 404 (M+); Calculated for C20H21ClN2O3S: C, 59.33; H, 5.23; N, 6.92. Found: C, 59.24; H, 5.22; N, 6.90.

Sources & evidence

ORD record
ord-b146038f0c65475b8a71c95ef15b942b
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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