3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → Benzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester

HRID 1766252Notes

Reaction equation

HRID 1766252 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([OH:27])[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1.[OH-].[Na+]>C1COCC1>[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 10270511Benzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl esterYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 31, using benzenesulfonyl chloride (280 μL, 2.2 mmol), 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (418 mg, 1.8 mmol) in 0.2 N sodium hydroxide (10 mL, 2.0 mmol) and THF (6 mL) gave 650 mg of an off white solid. The crude product was recrystallized from ethyl acetate to give 505 mg (75%) of tan needles: mp=192-194° C.; MS(m/e): 370 (M+); Calculated for C20H22N2O3S: C, 64.84; H, 5.99; N, 7.56. Found: C, 64.92; H, 6.19; N, 7.67.

Workup

  1. customgave 650 mg of an off white solid
  2. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d55fe9cb9688431d8941e272a2e8d594
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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