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

HRID 628736Notes

Reaction equation

HRID 628736 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 666798285-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamideYield 65.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2797bd06be4a443ca482cf0f4168fbd8
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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