Toluene → HCID 66701426, compound

HRID 424906Notes

Reaction equation

HRID 424906 reaction equation
[C:1]1(=O)CCCC(=O)C1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11]C1.[OH-:15].[Na+].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH:9]1([NH:14][C:21]2[CH2:22][C:17]([CH3:1])([CH3:23])[CH2:18][C:19](=[O:15])[CH:20]=2)[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 2906CyclopentylamineHCID 104341,3-CyclohexanedioneHCID 14798Sodium Hydroxide

Product 1

HCID 66701426HCID 66701426, compound

Procedure

To a toluene solution (30 ml) of 1,3-cyclohexanedione (1.40 g, 10.0 mmol), cyclopentylamine (782 mg, 11.0 mmol) and boron trifluoride diethyl ether complex (1.56 g, 11.0 mmol) were added at room temperature and the mixture was stirred under reflux for 14 hours. After concentrating the liquid reaction mixture under reduced pressure, a 5% aqueous sodium hydroxide solution was added. The liquid reaction mixture was extracted with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography. Thus, the title compound was obtained as a yellow oily product (1.64 g). 1HNMR (400 MHz, CDCl3, δ ppm): 1.06 (6H, s), 1.77-1.96 (4H, m), 2.17 (4H, d, J=7.3 Hz), 2.36-2.46 (2H, m), 3.85-3.95 (1H, m).

Workup

  1. temperatureunder reflux for 14 hours
  2. concentrationAfter concentrating
  3. customthe liquid reaction mixture under reduced pressure
  4. customThe liquid reaction mixture
  5. extractionwas extracted with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-6bcb5836477442ecb9aaac1799515812
Source dataset
uspto-grants-2012_01
Patent number
US08106086B2

Reaction notes

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