Sodium Hydroxide → 488127-49-7

HRID 898113Notes

Reaction equation

HRID 898113 reaction equation
[CH3:1][C:2]1([CH3:22])[O:10][C@@H:9]2[C@@H:4]([CH2:5][O:6][C@@:7]3([CH2:16][O:17][S:18]([NH2:21])(=[O:20])=[O:19])[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@H:8]32)[O:3]1.[OH-].[Na+:24]>O>[CH3:1][C:2]1([CH3:22])[O:10][C@@H:9]2[C@@H:4]([CH2:5][O:6][C@@:7]3([CH2:16][O:17][S:18]([NH-:21])(=[O:20])=[O:19])[O:13][C:12]([CH3:14])([CH3:15])[O:11][C@H:8]32)[O:3]1.[Na+:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5284627Topiramate

Product 1

HCID 23663532488127-49-7Yield 2.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

10.09 g (29.73 mmoles) of topiramate (Cheminor Drugs Ltd., Hyderabad, India, Batch TP001 J00) was placed in a 250 mL beaker and 100.0 mL of HPLC grade water (JT Baker, Phillipsburg, N.J. USA, Lot V32E17) was added. 1.36 g (34.0 mmoles) of sodium hydroxide (Sigma, St. Louis, Mo. USA, Lot 99H0120) was added and the mixture was stirred with a TEFLON® coated magnetic stir bar using a hot plate/stir plate. The mixture was heated to 60° C. to dissolve. The solution was filtered and evaporated at 60° C. while blowing air over the surface using a TYGON tube attached to an air source to reduce the volume to 15 mL, and the flask was placed in a cold room (4° C.) overnight. Crystals grew overnight. The mixture was filtered and dried to yield 305 mg topiramate sodium as large, block-like crystals. Elemental analysis: calc. C, 34.70, H, 6.31, N, 3.37%; found C, 34.90; H, 6.04; N, 3.36%. mp 80-85° C., recrystallization from melted material 110-120° C., second mp 170-175° C. PXRD Cu-Kα radiation (1.5406 Å) first 8 peaks (peak number/2Θ value), #1/4.51°, #2/12.09°, #3/12.709°, #4/13.67°, #5/15.01°, #6/16.17°, #7/17.19°, #8/17.55°. The pH of a 400 mg/mL solution of the compound in distilled water was about 11.2, which was determined using a Thermo Orion pH meter, Model 525A+ (Orion Research, Inc., Beverly, Mass. USA).

Workup

  1. additionwas added
  2. dissolutionto dissolve
  3. filtrationThe solution was filtered
  4. customevaporated at 60° C.
  5. customwas placed in a cold room (4° C.) overnight
  6. filtrationThe mixture was filtered
  7. customdried

Sources & evidence

ORD record
ord-5856345aa1514e5eb77d53ab891ff4de
Source dataset
uspto-grants-2008_04
Patent number
US07351695B2

Reaction notes

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