Dimethylformamide → 1-(2-Pyrazinyl)-4-piperidinone

HRID 580042Notes

Reaction equation

HRID 580042 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].O1[C:18]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[O:17]CC1.CN(C)C=O>O>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[N:21]1[CH2:22][CH2:23][C:18](=[O:17])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 73277Chloropyrazine

Product 1

HCID 141563981-(2-Pyrazinyl)-4-piperidinoneYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20 g (0.1746 mol) of chloropyrazine, 36 g (0.260 mol) of K2CO3, 76 g (0.5308 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, and 80 ml of dimethylformamide is stirred at 100° C. for 3 days. The reaction mixture is cooled, siluted with water, and extracted with ethyl acetate. The combined extracts are washed with water, dried over Na2SO4 and concentrated in vacuo. The residue, 400 ml of 10% sulfuric acid solution and 100 ml of tetrahydrofuran is stirred at ambient temperature for 4 days, diluted with water, basified with sodium hydroxide and extracted with methylene chloride. The extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Trituration with ether gives 8.4 g of title compound: IR (KBr) 1720 and 1580 cm-1 ; NMR (CDCl3) δ8.24-7.88 (m, 3H), 3.98 (t, 4H), and 2.56 (t, 4H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. stirringThe residue, 400 ml of 10% sulfuric acid solution and 100 ml of tetrahydrofuran is stirred at ambient temperature for 4 days
  7. additiondiluted with water
  8. extractionextracted with methylene chloride
  9. washThe extracts are washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c2902b3f7d44ad5b6443ad48fb2458c
Source dataset
uspto-grants-1988_06
Patent number
US04751305

Reaction notes

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