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

HRID 1753956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753956
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-ab32c9a6681c4a6382d21a82d003e01d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168317B2

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