Water → 3,4-Didehydronaratriptan

HRID 1028419Notes

Reaction equation

HRID 1028419 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)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]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)[NH:13][CH:12]=[C:11]2[C:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH:20]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 134757652-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

Product 1

HCID 200667343,4-Didehydronaratriptan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62.5 °C

Procedure

2-(1H-indol-5-yl)-ethanesulfonic acid methylamide (100 g) was dissolved in methanol (1000 ml) and N-methyl-4-piperidone (200 ml) was added thereto at 25° C. The reaction mass was stirred for 15 minutes and potassium hydroxide (300 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 (1500 ml) was added slowly and stirred the mixture till solid was obtained. The solid was filtered and dried at 50-55° C. under vacuum to obtain the title compound. (Yield: 80 g, HPLC Purity: 99%)

Workup

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

Sources & evidence

ORD record
ord-0c9d0acc77344e7486c8d8c8c8c5823c
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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