3,4-dihydro-2H-pyran → N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

HRID 356224

Reaktionsgleichung

Reaktionsgleichung von HRID 356224
[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 516892Sodium BicarbonateHCID 18941473N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline

Produkt 1

HCID 18941483N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

14.7 g (60.3 mmols) of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline, 90 ml of chloroform, 10.68 ml (2.0-fold equivalent weight) of 3,4-dihydro-2H-pyran and 0.76 g (0.05-fold equivalent weight) of pyridine p-toluenesulfonate were mixed, and the mixture obtained was heated at 70° C. for 1.5 hours in an atmosphere of argon. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution obtained, which was then extracted with chloroform (200 ml×2). The organic layer thus formed was washed with a saturated aqueous sodium hydrogencarbonate solution, which was then dried with anhydrous magnesium sulfate and thereafter concentrated. The residue thus obtained was purified by silica gel column chromatography (developing system: chloroform) to obtain 18.90 g of N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline (yield: quantitative; a colorless oily liquid).

Aufarbeitung

  1. customthe mixture obtained
  2. customobtained
  3. extractionwhich was then extracted with chloroform (200 ml×2)
  4. customThe organic layer thus formed
  5. washwas washed with a saturated aqueous sodium hydrogencarbonate solution, which
  6. dry with materialwas then dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (developing system: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-b2c959a9a8bd4a0dac1f7aab1d432dec
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834575

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