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

HRID 2112261Notes

Reaction equation

HRID 2112261 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>CN(C)C=O.O>[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

7

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 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

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 20 ml of N,N-dimethylformamide, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred at 90° C. for 10 hours. 100 ml of water was added to the reaction mixture. 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 1.93 g of title compound (yield 66%).

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried
  3. stirringstirred for 3 hours
  4. filtrationfiltered
  5. customdried under a reduced pressure

Sources & evidence

ORD record
ord-cd790513ff8840ff98dcdd43561e8023
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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