Trifluoroacetic acid → 3-chloro-4-fluoro-N-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-benzenesulfonamide

HRID 2180173

Reaktionsgleichung

Reaktionsgleichung von HRID 2180173
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([Cl:33])[CH:27]=2)(=[O:25])=[O:24])([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:28]1[CH:27]=[C:26]([S:23]([NH:22][CH2:21][C:11]2([C:14]3[CH:15]=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)(=[O:25])=[O:24])[CH:31]=[CH:30][C:29]=1[F:32]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 685333514-[(3-Chloro-4-fluoro-benzenesulfonylamino)-methyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 224903833-chloro-4-fluoro-N-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-benzenesulfonamideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-[(3-chloro-4-fluoro-benzenesulfonylamino)-methyl]-4-(4-iodo-phenyl)-piperidine-1 carboxylic acid tert-butyl ester (0.09 g, 0.16 mmol) in CH2Cl2 (1.5 mL) at 0° C. was added TFA (0.5 mL, to give a 25% v/v solution). The mixture was stirred at room temperature for 3 h. TLC (4:1 hexanes/EtOAc) showed no starting material left. The solvent was removed by rotary evaporation and the resulting liquid was evaporated from toluene (2×10 mL), diluted with EtOAc (100 mL) and washed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, and dried under high vacuum for 1 h to give 3-chloro-4-fluoro-N-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-benzenesulfonamide as a reddish solid (0.021 g, ˜0.04 mmol). MS: 509/511 (M+1).

Aufarbeitung

  1. customto give a 25% v/v solution)
  2. waitleft
  3. customThe solvent was removed by rotary evaporation
  4. customthe resulting liquid was evaporated from toluene (2×10 mL)
  5. additiondiluted with EtOAc (100 mL)
  6. washwashed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customdried under high vacuum for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-936951b5a21e44608e7f623c39365bcb
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887889B2

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