2-Methylimidazole → Ondansetron

HRID 580435

Reaktionsgleichung

Reaktionsgleichung von HRID 580435
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>[CH3:20][N:10]1[C:9]2[CH2:8][CH2:7][CH:6]([CH2:5][N:23]3[CH:24]=[CH:25][N:26]=[C:22]3[CH3:21])[C:18](=[O:19])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Komponenten

4

Edukt 2

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

Produkt 1

HCID 4595OndansetronAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3-[(dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride (1.7 g) in water (17 ml) was treated with 2-methylimidazole (1.4 g) and then heated under reflux for 20 h. The cooled mixture was filtered and the residue washed with water (3×15 ml) to give crude product (1.7 g) m.p. 221°-221.5°. This material was recrystallized from methanol to give the title compound (1.4 g) m.p. 231°-232°.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 20 h
  3. filtrationThe cooled mixture was filtered
  4. washthe residue washed with water (3×15 ml)
  5. customto give crude product (1.7 g) m.p. 221°-221.5°
  6. customThis material was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-2a785185ca884565925e58c5ade25b05
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04753789

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