Benzoic acid, 4-fluoro-, ethyl ester → Ethyl 4-(1,4-diazepan-1-yl)benzoate

HRID 16884

Reaktionsgleichung

Reaktionsgleichung von HRID 16884
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CS(C)=O>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Komponenten

4

Edukt 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 68163Hexahydro-1,4-diazepine

Produkt 1

HCID 18425301Ethyl 4-(1,4-diazepan-1-yl)benzoateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl 4-fluorobenzoate (11.01 mL, 75 mmol) and 1,4-diazepane (30.0 g, 300.00 mmol) in DMSO (150 mL) warmed to 100° C. under nitrogen. The resulting solution was stirred at 100° C. for 24 h. The reaction mixture was cooled and evaporated to dryness. The reaction mixture was quenched with 2M NaOH (150 mL), extracted with EtOAc (3×75 mL), the organic layer was washed with saturated brine (100 ml), dried over MgSO4, filtered and evaporated to afford ethyl 4-(1,4-diazepan-1-yl)benzoate (17.43 g, 94%) as a colourless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. customThe reaction mixture was quenched with 2M NaOH (150 mL)
  4. extractionextracted with EtOAc (3×75 mL)
  5. washthe organic layer was washed with saturated brine (100 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b9a6b874fcf245d1b0d4ef4dc609fbaf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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