Diethylamine → 5-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamide

HRID 1506715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506715
C(O[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])C.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH2:17][CH3:18])[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])[CH3:15]

Komponenten

5

Edukt 2

HCID 8021DiethylamineHCID 458119Ethyl 5-methyl-2-oxocyclohexane-1-carboxylate

Produkt 1

HCID 666798285-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamideAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester (45) (5.9 g, 32 mmol), DMAP (1.12 g, 10 mmol) and diethylamine (4.7 g, 65 mmol, 6.7 mL) in toluene (90 mL) were heated at reflux for 4 days. The reaction was allowed to cool and the toluene was removed under reduced pressure to give a yellow oil. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g) to afford 4.4 g (65%) of 5-methyl-2-oxo-cyclohexanecarboxylic acid diethylamide (46) as a yellow oil. The structure was confirmed 1H NMR (300 MHz, CDCl3) δH 0.8-1.05 (9H, m, CH3 and N(CH2CH3)2), 1.05-2.10 (5H, m, 5-CH and 4- and 6-CH2), 2.15-2.80 (2H, m, 3-CH2), 2.95-3.55 (5H, m, 1-CH and N(CH2CH3)2).

Aufarbeitung

  1. temperatureat reflux for 4 days
  2. temperatureto cool
  3. customthe toluene was removed under reduced pressure
  4. customto give a yellow oil
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g)

Quellen und Nachweise

ORD-Eintrag
ord-a18cf294a02044b5872d086136027258
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09220795B2

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