Dimethylformamide → N-methoxyethyl piperidinesulfonamide

HRID 842242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842242
COCCN1CCC([S:15]([N:18]2[CH2:23][CH2:22][CH:21](OC3C=CC(OC(F)(F)F)=CC=3)[CH2:20][CH2:19]2)(=[O:17])=[O:16])(C(OC)=O)CC1.C(=O)([O-])[O-].[K+].[K+].[CH3:42][O:43][CH2:44][CH2:45]Br.C[N:48](C)C=O>>[CH3:42][O:43][CH2:44][CH2:45][NH:48][S:15]([N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)(=[O:16])=[O:17]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 22052656Methyl 1-(2-methoxyethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate

Produkt 1

HCID 22052572N-methoxyethyl piperidinesulfonamideAusbeute 50 %

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

Part I: Preparation of methyl 1-(2-methoxyethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. The unsubstituted piperidine sulfonamide from part H (3.0 g, 6.45 mmol) was dissolved in dry dimethylformamide (15 mL) and potassium carbonate (1.3 g, 9.7 mmol) and 2-bromoethyl methyl ether (908 uL, 9.7 mmol) were added. The reaction was stirred at 35° C. for sixteen hr and then concentrated in vacuo. The residue was taken up in ethyl acetate and filtered through Celite. The filtrate washed with water two times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) provided the N-methoxyethyl piperidine sulfonamide as a white solid (1.65 g, 50%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered through Celite
  3. washThe filtrate washed with water two times, saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4eee4e661bb942b1a3c9c3c6ff336b74
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372758B1

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