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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1028419Generated: October 31, 2026

Water → 3,4-Didehydronaratriptan

https://huagongshe.com/reaction/1028419

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium HydroxideHCID 14797—
Reactant1-Methyl-4-piperidoneHCID 74049—
Reactant2-(1H-Indol-5-yl)-N-methylethane-1-sulfonamideHCID 13475765—
SolventMethanolHCID 887—
Product3,4-DidehydronaratriptanHCID 20066734—

Reaction Conditions

Temperature62.5 °C

Reaction Steps

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%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735589B2
Source datasetuspto-grants-2014_05
ORD IDord-0c9d0acc77344e7486c8d8c8c8c5823c
Source noteuspto-grants-2014_05