Morpholine → Methyl 6-morpholin-4-yl-6-oxohexanoate

HRID 16719

Reaktionsgleichung

Reaktionsgleichung von HRID 16719
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:12]1([C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:10][CH3:11])=[O:9])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6994472Methyl adipate

Produkt 1

HCID 23088646Methyl 6-morpholin-4-yl-6-oxohexanoateAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Monomethyl adipate (3.20 g) is dissolved in chloroform (70 ml), and thereto are added morpholine (2.61 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.75 g) and triethylamine (3.04 g) under ice-cooling. The mixture is then stirred at room temperature for 19 hours. Ice-water is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively and dried over sodium sulfate. The solvent is removed by evaporation under reduced pressure to give methyl 6-morpholin-4-yl-6-oxohexanoate (4.63 g).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6a36167b4724149bcf3c1378124ecc7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737161B2

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