Hydrochloric Acid → Naratriptan hydrochloride

HRID 1028422Notes

Reaction equation

HRID 1028422 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]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:5])=[O:4].[ClH:24]>CO>[ClH:24].[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[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4440Naratriptan

Product 1

HCID 60875Naratriptan hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
7.5 °C

Procedure

2-[3-(1-Methyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide (Naratriptan base) (100 g) was dissolved in methanol (1500 ml) under stifling for 30 minutes to obtain a clear solution. The reaction mass was cooled to 5-10° C. and 20% aqueous hydrochloric acid was added till the pH of the reaction mass was adjusted to 1.0. The temperature of the reaction mass was raised to 25° C. and filtered. The solid was dried in vacuum chamber at 50-55° C. to obtain the title compound. (Yield: 90 g, HPLC Purity: 99.69%)

Workup

  1. customto obtain a clear solution
  2. temperatureThe temperature of the reaction mass was raised to 25° C.
  3. filtrationfiltered
  4. customThe solid was dried in vacuum chamber at 50-55° C.

Sources & evidence

ORD record
ord-7835c1e85cbe494bbe3060ad946a30f2
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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