Chlorotrimethylsilane → Ondansetron

HRID 2112268Notes

Reaction equation

HRID 2112268 reaction equation
CN1[CH2:7][N:6]([CH3:8])[CH2:5][N:4]([CH3:9])C1.Cl[Si](C)(C)C.[CH3:15][N:16]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24](=[O:29])[C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2.[CH3:30]C1NC=CN=1>C(#N)C.C1(C)C=CC=CC=1>[CH3:15][N:16]1[C:28]2[CH2:27][CH2:26][CH:25]([CH2:8][N:6]3[CH:7]=[CH:9][N:4]=[C:5]3[CH3:30])[C:24](=[O:29])[C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 79521,3,5-Trimethyl-1,3,5-triazacyclohexaneHCID 127492-MethylimidazoleHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 4595OndansetronYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To the solution 19.5 g of 1,3,5-trimethylhexahydro-1,3,5-triazine in 20 ml of actonitrile and 150 ml of toluene, was slowly added 19 ml of chlorotrimethylsilane, which was then stirred for 10 min. 10 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one and 8.2 g of 2-methyl imidazole was subsequently added to the reaction mixture, which was then stirred under reflux. After completion of reaction, the reaction mixture was evaporated, and then 200 ml of water was added to the resulting residue, which was then stirred for 2 hours at room temperature. The resulting solid was filtered and washed with water to give 7.95 g of light yellow title compound (yield 54%).

Workup

  1. stirringwas then stirred
  2. temperatureunder reflux
  3. customAfter completion of reaction
  4. customthe reaction mixture was evaporated
  5. addition200 ml of water was added to the resulting residue, which
  6. stirringwas then stirred for 2 hours at room temperature
  7. filtrationThe resulting solid was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-df8577f54fd841fe8d572290c581f89a
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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