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Water → 1-(1-(2-Ethyl-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-(methylsulfonyl)piperazine

HRID 419598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 419598
[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1F)[CH3:2].Cl.Cl.[CH3:17][S:18]([N:21]1[CH2:26][CH2:25][N:24]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:23][CH2:22]1)(=[O:20])=[O:19].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:30]1[CH2:29][CH2:28][CH:27]([N:24]2[CH2:25][CH2:26][N:21]([S:18]([CH3:17])(=[O:20])=[O:19])[CH2:22][CH2:23]2)[CH2:32][CH2:31]1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 594528471-Ethyl-2-fluoro-4-methoxy-5-nitrobenzeneHCID 666497911-(Methylsulfonyl)-4-(4-piperidinyl)piperazine dihydrochloride

Produkt 1

HCID 594529781-(1-(2-Ethyl-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-(methylsulfonyl)piperazineAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-ethyl-2-fluoro-4-(methyloxy)-5-nitrobenzene (Example 187, step C) (0.93 g, 4.67 mmol), 1-(methylsulfonyl)-4-(4-piperidinyl)piperazine (Example 204, step C) (1.16 g, 4.67 mmol) and K2CO3 (0.774 g, 5.60 mmol) in DMSO (20 mL) was heated at 90° C. for 48 h. The reaction had not progressed sufficiently so the reaction was then heated at 120° C. for an additional 4 h. The reaction was cooled to rt, poured into H2O and extracted with DCM. Some saturated brine solution was added and the resultant was exhaustively extracted with DCM. The combined organics were washed with H2O then dried over MgSO4. The resultant solution was concentrated onto silica and purified by flash chromatography to afford 1-{1-[2-ethyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.12 g, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73-7.80 (m, 1H), 6.75 (s, 1H), 3.91 (s, 3H), 3.23-3.30 (m, 1H), 3.05-3.19 (m, 3H), 2.87 (s, 2H), 2.70-2.84 (m, 2H), 2.53-2.67 (m, 5H), 1.77-1.94 (m, 2H), 1.48-1.67 (m, 2H), 1.19 (t, J=7.42 Hz, 3H).

Aufarbeitung

  1. temperaturewas then heated at 120° C. for an additional 4 h
  2. temperatureThe reaction was cooled to rt
  3. extractionextracted with DCM
  4. additionSome saturated brine solution was added
  5. extractionthe resultant was exhaustively extracted with DCM
  6. washThe combined organics were washed with H2O
  7. dry with materialthen dried over MgSO4
  8. concentrationThe resultant solution was concentrated onto silica
  9. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd242b5d9fd548ddbf0125fad5e77dc9
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093239B2

Notizen zur Reaktion

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