2-Methylimidazole → Ondansetron

HRID 2112265

Reaction equation

HRID 2112265 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.N1(CN2CCCCC2)CCCC[CH2:23]1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C(#N)C.ClCCl>[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH:11]([CH2:23][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

8

Reactant 5

HCID 127492-MethylimidazoleHCID 14798Sodium HydroxideHCID 70151DipiperidinomethaneHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4595OndansetronYield 70%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2.0 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2-methyl imidazole and 274 g of dipiperidinomethane were suspended in 30 ml of acetonitrile, and then 2 g of aluminum chloride was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. 150 ml dichloromethane and 50 ml of 1N aq. sodium hydroxide were added to the reaction mixture. The resulting organic layer was separated and dried over MgSO4, and then evaporated. The resulting solid was suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 2.05 g of title compound (yield 70%).

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe resulting organic layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. stirringstirred for 3 hours
  6. filtrationfiltered
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-af9f12dbf1f24e54a0f9c9c78bf2726f
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Linked notes

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