Potassium Carbonate → 1-(2-Morpholin-4-ylethyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494179
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C.O>[N:23]1([CH2:22][CH2:21][N:11]2[C:12]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=3)[CH2:8][CH2:9][CH2:10]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineHCID 111491684-(2-iodoethyl)morpholine

Produkt 1

HCID 588741181-(2-Morpholin-4-ylethyl)-7-nitro-1,2,3,4-tetrahydroquinolineAusbeute 7,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (246 mg, 1.38 mmol) in DMF (2.7 ml) was added potassium carbonate (574 mg, 4.15 mmol) followed by a solution of 4-(2-iodoethyl)morpholine (500 mg, 2.07 mmol) in DMF (2 ml) and the reaction heated to 70° C. After cooling to ambient temperature the reaction mixture was diluted with water and extracted with EtOAc which was washed with water, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 80% EtOAc/petroleum ether gave the title compound as an orange gum (29 mg). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.39 (m, 2H), 7.00 (d, 1H), 3.73 (m, 4H), 3.47 (m, 2H), 3.38 (m, 2H), 2.79 (t, 2H), 2.49-2.59 (m, 6H), 1.96 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature the reaction mixture
  2. extractionextracted with EtOAc which
  3. washwas washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by silica SPE chromatography
  8. washElution with 80% EtOAc/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-c1f11253054c41899e4cbefe6415ca3c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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