Acetonitrile → 1-[4-(Trifluoromethyl)phenyl]-4-piperidinone

HRID 1382852Notes

Reaction equation

HRID 1382852 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O1[C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[O:21]CC1.C(#N)C>O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:25]2[CH2:26][CH2:27][C:22](=[O:21])[CH2:23][CH2:24]2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 212736221-[4-(Trifluoromethyl)phenyl]-4-piperidinoneYield 2.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g (0.1523 mol) of p-fluorobenzotrifluoride, 31 g (0.224 mol) of K2CO3, 65 g (0.4539 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, and 150 ml of acetonitrile is stirred at reflux for 3 days. The reaction mixture is cooled, diluted with water, and extracted with methylene chloride. The combined extracts are washed with water, dried over Na2SO4 and concentrated in vacuo. The residue, 600 ml of 10% sulfuric acid solution and 300 ml of tetrahydrofuran is stirred at ambient temperature for 7 days, diluted with water and extracted with methylene chloride. The extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Trituration with ether gives 0.9 g of title compound: IR (KBr) 1715, 1610, 1520 and 1330 cm-1 ; NMR (CDCl3) δ7.55 (d, 2H), 6.95 (d, 2H)m 3.73 (t, 4H), and 2.59 (t, 4H).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe combined extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. stirringThe residue, 600 ml of 10% sulfuric acid solution and 300 ml of tetrahydrofuran is stirred at ambient temperature for 7 days
  8. additiondiluted with water
  9. extractionextracted with methylene chloride
  10. washThe extracts are washed with brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0d057e655b947ca951ed6ff2be6b8d0
Source dataset
uspto-grants-1989_02
Patent number
US04808612

Reaction notes

Loading…