Sodium Iodide → (4-Bromo-3-methyl-phenyl)-(2-morpholin-4-yl-ethyl)-amine

HRID 723192

Reaktionsgleichung

Reaktionsgleichung von HRID 723192
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[CH3:9]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 233594-Bromo-3-methylanilineHCID 767274-(2-Chloroethyl)morpholine

Produkt 1

HCID 21886410(4-Bromo-3-methyl-phenyl)-(2-morpholin-4-yl-ethyl)-amineAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Bromo-3-methylaniline (0.96 gm, 5.14 mmol), 4-(2-chloro-ethyl)-morpholine (1 gm, 5.4 mmol), K2CO3 (1.5 gm, 10.8 mmol), and NaI (0.81 gm, 5.4 mmol) were suspended in DMSO (10 mL) and the mixture was stirred vigorously at reflux for 12 h. The mixture was cooled, diluted with EtOAc, and washed with saturated NaHCO3. The organic layer was washed with another portion of NaHCO3, brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue (Biotage Flash System—40 M SiO2 column, 10% EtOAc in hexanes to 100% EtOAc) yielded the product (500 mg, 31%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.36 (d, 1H, J=8.6 Hz), 6.61 (d, 1H, J=2.8 Hz), 6.43 (dd, 1H, d, 8.6, 2.8 Hz), 4.36 (br s, 1H), 3.80 (t, 4H, J=4.6 Hz), 3.20 (t, 2H, J=5.8 Hz), 2.69 (t, 2H, J=6.0 Hz), 2.54 (t, 4H, J=4.4 Hz), 2.40 (s, 3H). ESI-MS (m/z): Calcd. for C13H19BrN2O: 299.2; found: 299.1, 301.1.

Aufarbeitung

  1. temperatureat reflux for 12 h
  2. temperatureThe mixture was cooled
  3. washwashed with saturated NaHCO3
  4. washThe organic layer was washed with another portion of NaHCO3, brine (50 mL)
  5. dry with materialwas dried over MgSO4
  6. customRemoval of the solvents in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4c975158b43140fd95df4e953d3591dc
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138530B2

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