Potassium Iodide → 4-(4-Methoxy-3,5-dimethylphenyl)-1-[(4-methylphenyl)sulfonyl]piperazine

HRID 266065

Reaktionsgleichung

Reaktionsgleichung von HRID 266065
Cl.[CH3:2][O:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([NH2:11])=[CH:6][C:5]=1[CH3:12].Cl[CH2:14][CH2:15][N:16]([CH2:27][CH2:28]Cl)[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].C1(O)CCCCC1>O>[CH3:2][O:3][C:4]1[C:5]([CH3:12])=[CH:6][C:7]([N:11]2[CH2:28][CH2:27][N:16]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH2:15][CH2:14]2)=[CH:8][C:9]=1[CH3:10]

Komponenten

7

Edukt 5

HCID 4875Potassium IodideHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 190323804-Methoxy-3,5-dimethylaniline HCl

Produkt 1

HCID 190323874-(4-Methoxy-3,5-dimethylphenyl)-1-[(4-methylphenyl)sulfonyl]piperazineAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 10 g of 4-methoxy-3,5-dimethylbenzenamine hydrochloride, 19.9 g of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide, 16.8 g of sodium carbonate, 0.5 g of potassium iodide and 100 ml of cyclohexanol was stirred overnight at 150°-160° C. After cooling, the reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 1-butanol, yielding 10 g (50.4%) of 4-(4-methoxy-3,5-dimethylphenyl)-1-[(4-methylphenyl)sulfonyl]piperazine; mp. 174.2° C. (interm. 42).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe product was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column-chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from 1-butanol

Quellen und Nachweise

ORD-Eintrag
ord-defd8b78b9dd4aa5ae0b400304ec643c
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650411

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