Water → Ondansetron

HRID 11812

Reaction equation

HRID 11812 reaction equation
Cl.CN([CH2:5][CH:6]1[C:18](=[O:19])[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:20])[C:9]=2[CH2:8][CH2:7]1)C.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.O>CN(C)C=O>[CH3:21][C:22]1[N:26]([CH2:5][CH:6]2[C:18](=[O:19])[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]([CH3:20])[C:9]=3[CH2:8][CH2:7]2)[CH:25]=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 127492-MethylimidazoleHCID 219769253-[(Dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride

Product 1

HCID 4595OndansetronYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(Dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride (10 g, 34 mmol) and 2-methylimidazole (16.8 g, 205 mmol, 6.0 eq.) were suspended in mixture of water (75 ml) and dimethyl formamide (37.5 ml). The reaction mixture was heated to reflux (102–103° C.) and stirred for a further 6 hours at this temperature. The reaction mixture was cooled to 5–10° C. and stirred for half an hour at this temperature. The precipitated crude ondansetron base was filtered and washed with cold water (3×90 ml) and dried under vacuum at 60° C. to give ondansetron base (9.68 g, 96.4% yield) in 98.9% HPLC purity.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux (102–103° C.)
  3. temperatureThe reaction mixture was cooled to 5–10° C.
  4. stirringstirred for half an hour at this temperature
  5. customThe precipitated crude ondansetron base
  6. filtrationwas filtered
  7. washwashed with cold water (3×90 ml)
  8. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-c6bf3ab9737a4f4b86487ecc57403964
Source dataset
uspto-grants-2006_08
Patent number
US07098345B2

Linked notes

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