Water → Sumatriptan Succinate

HRID 1797389

Reaction equation

HRID 1797389 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].O.[C:22]([OH:29])(=[O:28])[CH2:23][CH2:24][C:25]([OH:27])=[O:26]>C(#N)C>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[CH2:23]([C:22]([OH:29])=[O:28])[CH2:24][C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 5358Sumatriptan

Product 1

HCID 59772Sumatriptan Succinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sumatriptan (10.0 grams), water (50.0 ml), succinic acid (3.99 grams) and acetonitrile (100.0 ml) were heated to reflux temperature. The reaction mass was stirred for 15–30 minutes at reflux and filtered in hot condition. The solvent was distilled off completely from the filtrate under reduced pressure at a temperature of below 35–45° C. Cyclohexane (100 ml) was added to the resulting residual mass and stirred for 1–2 hours at a temperature of 25–35° C. to crystallize the solid. Then the solid was filtered, washed with cyclohexane (50 ml) and on subsequent drying under vacuum at a temperature of 25–35° C. there resulted the amorphous form of Sumatriptan succinate of the invention.

Workup

  1. temperatureto reflux temperature
  2. temperatureat reflux
  3. filtrationfiltered in hot condition
  4. distillationThe solvent was distilled off completely from the filtrate under reduced pressure at a temperature of below 35–45° C
  5. additionCyclohexane (100 ml) was added to the resulting residual mass
  6. stirringstirred for 1–2 hours at a temperature of 25–35° C.
  7. customto crystallize the solid
  8. filtrationThen the solid was filtered
  9. washwashed with cyclohexane (50 ml)
  10. customon subsequent drying under vacuum at a temperature of 25–35° C.

Sources & evidence

ORD record
ord-45b04b78ce9c47cbb51f67d772a3c1ec
Source dataset
uspto-grants-2006_04
Patent number
US07034162B2

Linked notes

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