Morpholine → N-(2,5-Dimethylphenyl)morpholine

HRID 227848

Reaktionsgleichung

Reaktionsgleichung von HRID 227848
CC([O-])(C)C.[Na+].Br[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH3:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 11052463N-(2,5-Dimethylphenyl)morpholineAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (13.9 mg, 0.015 mmol, 3.0 mol % Pd), 2 [Example 1] (17.9 mg, 0.045 mmol, 4.5 mol %), and NaOt-Bu (140 mg, 1.4 mmol). The tube was purged with argon, fitted with a rubber septum and then DME (0.5 mL), 2-bromo-p-xylene (140 μL, 1.01 mmol) and morpholine (105 μL, 1.2 mmol) were added via syringe. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 24 h. The reaction mixture was then diluted with ether (20 mL), filtered through celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 185 mg (95%) of a colorless oil.

Aufarbeitung

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customThe tube was purged with argon
  3. customfitted with a rubber septum
  4. customThe septum was removed
  5. customthe tube was sealed with a teflon
  6. customscrew cap
  7. additionThe reaction mixture was then diluted with ether (20 mL)
  8. filtrationfiltered through celite and
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cd927df962af4339be37943796b0e34d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560582B2

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