Morpholine → HCID 15058492, Verbindung

HRID 1087317

Reaktionsgleichung

Reaktionsgleichung von HRID 1087317
Br[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C.Cl>[O:18]1[CH2:19][CH2:20][N:15]([CH:2]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:16][CH2:17]1

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 4737529Ethyl 2-bromo-3-phenylpropanoate

Produkt 1

HCID 15058492HCID 15058492, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.0 g ethyl 2-bromo-3-phenylpropionate and 2.8 g morpholine in 5 mL DMF was stirred overnight at RT. The mixture was diluted with 75 mL 1% HCl and washed 3×50 mL ether. The aqueous phase was made basic and extracted 3×100 mL EtOAc. The combined extracts were dried over MgSO4, filtered and concentrated. The residue was chromatographed (35% EtOAc:Hex) to afford 0.8 g pure product. NMR (300 MHz, CDCl3) delta 1.12 (t, J=7 Hz, 3H), 3.36 (m, 1H), 4.04 (m, 2H).

Aufarbeitung

  1. washwashed 3×50 mL ether
  2. extractionextracted 3×100 mL EtOAc
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed (35% EtOAc:Hex)

Quellen und Nachweise

ORD-Eintrag
ord-4876e307f9bc4ee59ce7cec23c89fef7
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034376

Verknüpfte Notizen

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