Benzene → 4-[4-[[4-[(6-Chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]phenyl]-1-methylpyridinium iodide

HRID 352901Notes

Reaction equation

HRID 352901 reaction equation
[CH:1]1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([S:18]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:40])[C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)[CH2:23][CH2:22]1)(=[O:20])=[O:19])[CH:12]=[CH:11]2.C[I:42]>CO>[I-:42].[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([S:18]([N:21]1[CH2:26][CH2:25][N:24]([C:27]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:39]=[CH:38][N+:37]([CH3:1])=[CH:36][CH:35]=4)=[CH:32][CH:33]=3)=[O:40])[CH2:23][CH2:22]1)(=[O:20])=[O:19])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 6328Methyl iodide2×HCID 99572891-[(6-Chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine

Product 1

HCID 227108464-[4-[[4-[(6-Chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]phenyl]-1-methylpyridinium iodideYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixed solvent of benzene (10 ml) and methanol (10 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine (300 mg) obtained in Example A-1 was dissolved at room temperature, followed by the addition of methyl iodide (1 ml). To the resulting mixture, the same amount of methyl iodide was added three times at intervals of 24 hours, followed by heating under reflux for 4 days. The reaction mixture was distilled under reduced pressure and the residue was washed with methanol, collected by filtration and dried, whereby the title compound (229 mg, 58%) was obtained as a yellow solid.

Workup

  1. dissolutionwas dissolved at room temperature
  2. temperatureby heating
  3. temperatureunder reflux for 4 days
  4. distillationThe reaction mixture was distilled under reduced pressure
  5. washthe residue was washed with methanol
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-4a5bc9df6c1543eba5c8cb12c49251a5
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…