N,N,N',N'-Tetramethylmethanediamine → Zofran

HRID 2112271Notes

Reaction equation

HRID 2112271 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].CN(CN(C)C)C.[CH3:12][N:13]1[C:25]2[CH2:24][CH2:23][CH2:22][C:21](=[O:26])[C:20]=2[C:19]2[C:14]1=C[CH:16]=[CH:17][CH:18]=2.[CH3:27][C:28]1[NH:29][CH:30]=[CH:31][N:32]=1>C(#N)C>[OH2:3].[OH2:26].[ClH:4].[CH3:12][N:13]1[C:14]2[CH2:19][CH2:18][CH:17]([CH2:16][N:29]3[CH:30]=[CH:31][N:32]=[C:28]3[CH3:27])[C:1](=[O:3])[C:2]=2[C:20]2[C:25]1=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

6

Reactant 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chlorideHCID 127492-MethylimidazoleHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 59774ZofranYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of 11 ml of acetyl chloride in 350 ml of actonitrile, was slowly added 21 ml of N,N,N′,N′-tetramethyldiaminomethane at 0° C., which was then stirred for 10 min. 20 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one and 50 g of 2-methyl imidazole was subsequently added to the reaction mixture under reflux. After completion of reaction, the resulting solid was filtered and washed with acetonitrile and water, and then dried. The resulting solid was suspended in 250 ml of ethanol, and 11 ml of conc. HCl was slowly added thereto, which was then stirred for 2 hours. The resulting solid was filtered and washed with cold ethanol, and then re-crystallized with water to give 28.3 g of pure white title compound (yield 78%).

Workup

  1. customat 0° C.
  2. temperatureunder reflux
  3. customAfter completion of reaction
  4. filtrationthe resulting solid was filtered
  5. washwashed with acetonitrile and water
  6. customdried
  7. addition11 ml of conc. HCl was slowly added
  8. stirringwhich was then stirred for 2 hours
  9. filtrationThe resulting solid was filtered
  10. washwashed with cold ethanol
  11. customre-crystallized with water

Sources & evidence

ORD record
ord-2f2587478b384bdb81a09a72337be3c3
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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