Potassium Iodide → 1-(5-Iodo-2-methyl-phenyl)-4-(toluene-4-sulfonyl)-piperazine

HRID 657488Notes

Reaction equation

HRID 657488 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:15][CH2:16]Cl)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+].[I:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:34])=[C:31]([CH:33]=1)[NH2:32]>C1(O)CCCCC1>[I:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:34])=[C:31]([N:32]2[CH2:16][CH2:15][N:4]([S:5]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:3][CH2:2]2)[CH:33]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 5228025-Iodo-o-toluidine

Product 1

HCID 595639611-(5-Iodo-2-methyl-phenyl)-4-(toluene-4-sulfonyl)-piperazineYield 96.9%

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Procedure

9.97 g of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (30.3 mmol) and 5.03 g of potassium iodide (30.3 mmol) in 75 mL of cyclohexanol were stirred for 1 h at 80° C. After addition of 7.7 g of sodium carbonate (72.7 mmol) and 5.65 g of 5-iodo-2-methyl-aniline (24.2 mmol), stirring continued for 8 h at 160° C. At room temperature, the mixture was filtered, washed with dichloromethane, and the filtrate evaporated to dryness. The residue was dissolved in dichloromethane, filtered, and the solvent evaporated. The remaining residue was trituated with n-heptane and the crystalline product filtered off, washed several times with n-heptane and dried in vacuo to yield 10.7 g of product.

Workup

  1. filtrationAt room temperature, the mixture was filtered
  2. washwashed with dichloromethane
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. filtrationthe crystalline product filtered off
  8. washwashed several times with n-heptane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-cf77862f379844cf8287a78280910f5e
Source dataset
uspto-grants-2011_12
Patent number
US08076326B2

Reaction notes

Loading…