N,N,N',N'-Tetramethylmethanediamine → Ondansetron

HRID 2112260Notes

Reaction equation

HRID 2112260 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH3:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1.[CH3:22]N(CN(C)C)C.Cl[Si](C)(C)C>C(#N)C>[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH:11]([CH2:22][N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[CH3:16])[C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6397ChlorotrimethylsilaneHCID 127492-MethylimidazoleHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 4595OndansetronYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.0 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2-methyl imidazole and 2 ml of N,N,N′,N′-tetramethyldiaminomethane were suspended in 30 ml of acetonitrile, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 40 ml of water was added to the resulting residue. The resulting solid was filtered and dried, which was then suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 1.76 g of title compound (yield 60%).

Workup

  1. temperatureunder reflux for 10 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the solvent
  4. addition40 ml of water was added to the resulting residue
  5. filtrationThe resulting solid was filtered
  6. customdried
  7. stirringstirred for 3 hours
  8. filtrationfiltered
  9. customdried under a reduced pressure

Sources & evidence

ORD record
ord-78a4c3d8154d4c0bb9af3d22bbe99714
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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