Water → Ondansetron

HRID 11813

반응식

HRID 11813 반응식
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=O)C>[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

참가 물질

5

반응물 3

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

생성물 1

HCID 4595Ondansetron수율 83.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-[(Dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride (12 kg, 41 mol) and 2-methylimidazole (20.2 kg, 246 mol, 6 eq.) were suspended in mixture of water (120 L) and DMF (30 L). The reaction mixture was heated to reflux (100–102° C.) and stirred for 5 hours at this temperature. The reaction mixture was cooled to 5–10° C. and stirred for half an hour. The precipitated crude ondansetron base was filtered and washed with cold water (2×110 L) and dried under vacuum at 60° C. to give ondansetron base (10 kg, 83% yield) in 97.3% HPLC purity. The major impurity was the exomethylene carbazolone which amounted to 2.6% of the crude ondansetron mixture.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux (100–102° C.)
  3. temperatureThe reaction mixture was cooled to 5–10° C.
  4. stirringstirred for half an hour
  5. customThe precipitated crude ondansetron base
  6. filtrationwas filtered
  7. washwashed with cold water (2×110 L)
  8. customdried under vacuum at 60° C.

출처 및 근거

ORD 기록
ord-4fddb17bac00436194745b17dd4dce0d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098345B2

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