Potassium Hydroxide → Naratriptan

HRID 1028410Notes

Reaction equation

HRID 1028410 reaction equation
BrC1C=C2C(=[CH:9][CH:10]=1)NC=C2.CN1CCC(=O)CC1.[OH-].[K+].Br[C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[C:31]1[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH:36]=1.CC=[CH:40][NH:41][SH:42](=[O:44])=[O:43]>CO>[CH3:40][NH:41][S:42]([CH2:9][CH2:10][C:22]1[CH:30]=[CH:29][C:28]2[NH:27][CH:26]=[C:25]([CH:31]3[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]3)[C:24]=2[CH:23]=1)(=[O:44])=[O:43]

Participants

7

Reactant 5

HCID 14797Potassium HydroxideHCID 249055-BromoindoleHCID 740491-Methyl-4-piperidoneHCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 178458093HCID 178458093, compound

Product 1

HCID 4440Naratriptan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In another process as described in US '841, if the reaction of 5-bromoindole with 1-methylpiperidin-4-one by means of KOH in methanol is carried out at reflux temperature the resulting product is 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole which is further condensed with N-methylvinylsulfonamide as described above to obtain naratriptan.

Workup

  1. temperatureat reflux temperature the resulting product

Sources & evidence

ORD record
ord-c9bc2904248d4c50939eae5012f68ba4
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

Loading…