P-Toluenesulfonamide → N-[4-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-1-oxobutyl]-4-methyl-benzenesulfonamide

HRID 915548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915548
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:9][CH2:8]1.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:28][CH:29]=1.CN(C1C=CC=CN=1)C.CCN=C=NCCCN(C)C>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][C:16]([NH:33][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=2)(=[O:31])=[O:32])=[O:18])[CH2:11][CH2:12]1

Komponenten

6

Edukt 4

HCID 6269P-ToluenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 694203114-(3,4-Dichlorophenoxy)-1-piperidinebutanoic acid hydrochloride

Produkt 1

HCID 69418750N-[4-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-1-oxobutyl]-4-methyl-benzenesulfonamideAusbeute 12,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(3,4-Dichlorophenoxy)-1-piperidinebutanoic acid hydrochloride (0.250 g) was dissolved in dichloromethane (10 mL) containing p-toluenesulfonamide (0.142 g), dimethylaminopyridine (92 mg) and EDCI (0.158 g) were added. The solution was stirred at room temperature for 4 days. The solvent was evaporated. The crude product was dried in vacuo and then purified by HPLC (at column dilution, gradient ammonium acetate/acetonitrile 75% to 5% ;Waters Xterra® column) and to give the title compound (42 mg).

Aufarbeitung

  1. additionwere added
  2. customThe solvent was evaporated
  3. dry with materialThe crude product was dried in vacuo
  4. custompurified by HPLC (at column dilution, gradient ammonium acetate/acetonitrile 75% to 5% ;Waters Xterra® column)

Quellen und Nachweise

ORD-Eintrag
ord-78a1118f2fe149669a35b69e2a69d9a9
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265227B2

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