Water → 2-[1-Benzyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]-N-methylethane-1-sulfonamide

HRID 1028421Notes

Reaction equation

HRID 1028421 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:12]=[CH:11]2)(=[O:5])=[O:4].[CH3:24][N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.[OH-].[K+].O>CO>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:12]=[C:11]2[C:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH:27]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 669739242-(1-Benzyl-1H-indol-5-yl)-N-methylethane-1-sulfonamide

Product 1

HCID 299839712-[1-Benzyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]-N-methylethane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62.5 °C

Procedure

2-(1-benzyl-1H-indol-5-yl)-ethanesulfonic acid methylamide (100 g) was dissolved in methanol (1000 ml) and N-methyl-4-piperidone (100 ml) was added thereto at 25° C. The reaction mass was stirred for 15 minutes and potassium hydroxide (200 g) was added at 25° C. The reaction mass was heated to 60-65° C. for 8 hours and cooled gradually to 25° C. Water (2500 ml) was added slowly and stirred the mixture till solid is obtained. The solid was filtered and dried at 50-55° C. under vacuum to obtain the title compound (Yield: 98 g, HPLC Purity: 99%).

Workup

  1. customat 25° C
  2. temperaturecooled gradually to 25° C
  3. stirringstirred the mixture till solid
  4. customis obtained
  5. filtrationThe solid was filtered
  6. customdried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-c142dc2283a4497eb649aa6d9f0cf864
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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