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Acetic Acid → HCID 15380922, Verbindung

HRID 610772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 610772
[H-].[H-].C[CH2-].C[CH2-].[Na+].[Al+3].[CH:9]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C[O:17][C:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].C(O)(=O)C>C1(C)C=CC=CC=1>[CH:9]1([NH:15][C:18](=[O:17])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7965CyclohexylamineHCID 87331Aluminate(1-), diethyldihydro-, sodium (1:1), (T-4)-HCID 15380921HCID 15380921, Verbindung

Produkt 1

HCID 15380922HCID 15380922, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of sodium diethyldihydroaluminate (4.44 ml, 8.9 mmole) in a concentration of 2 moles per liter in toluene, is added to a solution of cyclohexylamine (1.76 g, 2.03 ml, 18 mmole) in anhydrous toluene (60 ml). The reaction mixture is heated to 110° C. for 1 hour, then a solution of methyl-5-[benzyl{2-(2-methoxyphenoxy)ethyl}amino]pentanoate (6 g, 16 mmole) in toluene (25 ml) is added dropwise. The mixture is heated under reflux for 3 hours and left for 18 hours at 20° C., then neutralised with a 10% solution of acetic acid. The organic phase is extracted then washed successively with a saturated solution of sodium hydrogen carbonate then with water. After drying over magnesium sulfate and evaporation of the solvents under reduced pressure, the product is purified by flash chromatography over silica gel in a mixture of ethyl acetate/heptane (2/1). 3.3 g (47%) of the desired product are obtained in the form of an oil.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. extractionThe organic phase is extracted
  4. washthen washed successively with a saturated solution of sodium hydrogen carbonate
  5. dry with materialAfter drying over magnesium sulfate and evaporation of the solvents under reduced pressure
  6. customthe product is purified by flash chromatography over silica gel in a mixture of ethyl acetate/heptane (2/1)

Quellen und Nachweise

ORD-Eintrag
ord-770edc398db1457b94fddc89bc2351fa
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05998666

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