Cyanoacetamide → 5-Cyclopropyl-6-ethyl-1,2-dihydro-2-oxo-3-pyridinecarbonitrile

HRID 1938824Notes

Reaction equation

HRID 1938824 reaction equation
[CH:1]1([C:4]([C:12](=O)[CH2:13][CH3:14])=[CH:5]N2CCOCC2)[CH2:3][CH2:2]1.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].C(O)(=O)C.N1CCCCC1>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:18]([C:16]#[N:17])[C:19](=[O:20])[NH:21][C:12]=2[CH2:13][CH3:14])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 9793820Piperidine, acetateHCID 53970200HCID 53970200, compound

Product 1

HCID 214702275-Cyclopropyl-6-ethyl-1,2-dihydro-2-oxo-3-pyridinecarbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sample of 2-Cyclopropyl-1-(morpholin-4-yl)pent-1-en-3-one (2A, 2.09 g, 10 mmol), cyanoacetamide (0.92 g, 11 mmol) and piperidine acetate (4 mL) were dissolved in ethanol (30 mL) under nitrogen. The reaction mixture was heated at reflux for 24 hours. The reaction mixture was cooled and concentrated, then diluted with methylene chloride. The solution was washed with brine and dried (MgSO4), filtered and concentrated. The crude solid was chromatographed (silica, 5% methanol/methylene chloride) to afford pure title compound (3A, 1.54 g, 82%) as a crystalline solid. 1H NMR (300 MHz, CDCl3): δ0.62 (m, 2H), 0.98 (m, 2H), 1.38 (t, 3H), 1.71 (m, 1H), 2.91 (q, 2H), 7.63 (s, 1H); MS (DCI/NH3) m/e 189 (M+H)+, 206 (M+NH4)+. Anal. Calcd for C11 H12N2O: C, 70.19; H, 6.42; N, 14.88. Found C, 70.31; H, 6.49; N, 14.62.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. additiondiluted with methylene chloride
  6. washThe solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude solid was chromatographed (silica, 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-947908f8d41b40e0a343556c95bdd950
Source dataset
uspto-grants-1997_12
Patent number
US05693813

Reaction notes

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