Methylamine → HCID 54319478, Verbindung

HRID 1581115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1581115
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=O.[CH3:26][NH2:27].[O-]CC.[Na+].[Na]>C(O)C>[CH3:26][NH:27][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:3]1[CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:5][CH2:6][CH:2]1[OH:1]

Komponenten

6

Edukt 4

HCID 6329MethylamineHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

Produkt 1

HCID 54319478HCID 54319478, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel4×

Versuchsvorschrift

To a solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (0.8 g.) [prepared as described in Example 5] in ethanol (16 ml.) was added 33% methylamine in ethanol (4 ml.) followed by sodium ethoxide in ethanol [0.8 ml. of a solution prepared by dissolving sodium (0.2 g.) in ethanol (1 ml.)]. The resulting solution was refluxed for 1 day and the ethanol removed in vacuo. The residue was diluted with ice-cooled water and extracted twice with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulphate and evaporated to give N-methyl-7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoamide (0.2g., 25%). Found: C, 71.9; H, 10.6. C21H39NO3 requires C, 71.4; H, 11.05%) νmax 3300 cm-1, 1650 cm-1, 1570 cm-1 and 980 cm-1 (liquid film).

Aufarbeitung

  1. customof a solution prepared
  2. temperatureThe resulting solution was refluxed for 1 day
  3. customthe ethanol removed in vacuo
  4. additionThe residue was diluted with ice-
  5. temperaturecooled water
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe combined dichloromethane extracts were dried over magnesium sulphate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fc9b39bdd1a3425f9aade680ccdda628
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03935261

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