Hydrochloric Acid → Zofran

HRID 642923

Reaction equation

HRID 642923 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH:8]2[C:21](=[O:22])[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[N:19]([CH3:20])[C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[ClH:23]>C(O)(C)C.O>[CH3:1][C:2]1[N:6]([CH2:7][CH:8]2[C:21](=[O:22])[C:12]3[C:13]4[C:18]([N:19]([CH3:20])[C:11]=3[CH2:10][CH2:9]2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:5]=[CH:4][N:3]=1.[OH2:22].[OH2:22].[ClH:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4595Ondansetron

Product 1

HCID 59774ZofranYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

The crude ondansetron from Example 4 (190 grams; 0.65 mol) was suspended in a mixture of isopropanol (1.2 L) and water (0.24 L). Concentrated hydrochloric acid (32% (w/w)) was added until the pH of the mixture was about 1-2 (about 70 mL). The solution was heated to reflux temperature for one hour and then cooled to room temperature. The precipitated crystals were collected by filtration, and dried to provide 117 grams (0.32 mol; 49% yield) of crude ondansetron hydrochloride dihydrate. The purity was determined to be about 98-99% by HPLC.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux temperature for one hour
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-0310217a65cb45f193e82b9f3ceb3ced
Source dataset
uspto-grants-2010_04
Patent number
US07696356B2

Linked notes

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