Potassium Hydroxide → (E)-N-Methyl-2-[3-(4-hydroxy-1-methyl-4-piperidinyl)-1H-indol-5-yl]ethenesulphonamide

HRID 2258134Notes

Reaction equation

HRID 2258134 reaction equation
[CH3:1][NH:2][S:3](/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1.[OH-].[K+]>CCOCC>[CH3:1][NH:2][S:3](/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:21]1([OH:24])[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 134757642-(1H-indol-5-yl)-N-methylethenesulfonamide

Product 1

HCID 19068423(E)-N-Methyl-2-[3-(4-hydroxy-1-methyl-4-piperidinyl)-1H-indol-5-yl]ethenesulphonamideYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (E)-N-methyl-2-(1H-indole-5-yl)ethenesulphonamide (2.0 g), 1-methyl-4-piperidone (1.62 g) and potassium hydroxide (0.7 g) in IMS (20 mL) was stirred at ambient temperature for 22 hr. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel. Eluting with dichloromethane/ethanol/ammonia (25:10:1) gave an oil which solidified on standing to a brown solid. Trituration with ether provided the product as a white powder (1.85 g, 64% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography on silica gel
  3. washEluting with dichloromethane/ethanol/ammonia (25:10:1)
  4. customgave an oil which

Sources & evidence

ORD record
ord-a98f55042771491cb8e73dff09c3e775
Source dataset
uspto-grants-1997_08
Patent number
US05659040

Reaction notes

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