Morpholine → 4-(1-(4-Nitrophenyl)ethyl)morpholine

HRID 1179228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179228
Br[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH3:3])=[CH:5][CH:6]=1)([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 110206791-(1-Bromoethyl)-4-nitrobenzene

Produkt 1

HCID 133988034-(1-(4-Nitrophenyl)ethyl)morpholineAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(1-bromo-ethyl)-4-nitro-benzene (1.24 g, 5.43 mmol), potassium carbonate (2.25 g, 16.3 mmol) and morpholine (1.2 mL, 13.6 mmol) in DMF (10 mL) was stirred at room temperature for 16 h, then evaporated. The residue was suspended in ethyl acetate, washed with water and brine, dried (sodium sulfate) and evaporated to provide 4-[1-(4-nitro-phenyl)-ethyl]-morpholine (1.225 g, 95% yield) as a yellow oil. 1H-NMR (DMSO-d6, 500 MHz) 8.19 (d, 2H), 7.16 (d, 2H), 3.56 (m, 5H), 2.41 (m, 2H), 2.26 (m, 2H), 1.29 (d, 3H) ppm; MS (FIA) 237.2 (M+H); HPLC (Method A) 2.248 min.

Aufarbeitung

  1. customevaporated
  2. washwashed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c94c1f28205849a09d15413d011c366a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279469B2

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