Acetyl chloride → Ondansetron

HRID 2112266Notes

Reaction equation

HRID 2112266 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.[C:16](Cl)(=O)[CH3:17].C[C:21]1[NH:22][CH:23]=[CH:24][N:25]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH:11]([CH2:21][N:22]3[CH:23]=[CH:24][N:25]=[C:16]3[CH3:17])[C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 127492-MethylimidazoleHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 4595OndansetronYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, 2 ml of N,N,N′,N′-tetramethyl- diaminomethane were suspended in 30 ml of toluene, and then 1.4 ml of acetyl chloride was slowly added thereto, which was then stirred for 10 min. 1.65 g of 2-methyl imidazole was added to the reaction mixture, which was then stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 150 ml dichloromethane and 50 ml of 1 N aq. sodium hydroxide were added to the resulting residue. The resulting organic layer was separated and dried over MgSO4, and then evaporated. The resulting solid was suspended in acetone, which was then stirred for 3 hours, and then filtered and dried to give 1.70 g of title compound (yield 58%).

Workup

  1. stirringwas then stirred
  2. temperatureunder reflux for 10 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the solvent
  5. addition150 ml dichloromethane and 50 ml of 1 N aq. sodium hydroxide were added to the resulting residue
  6. customThe resulting organic layer was separated
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. stirringwhich was then stirred for 3 hours
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-9de6906f8ffc42cbb6f39961a9ffaf74
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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