Sodium Carbonate → 1-(2-(5-Pyrimidinyl)-prop-2-yl)-4-oxopiperidine

HRID 2294944Notes

Reaction equation

HRID 2294944 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([NH2:10])([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[I-].C[N+]1(C)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)C>[N:1]1[CH:6]=[C:5]([C:7]([N:10]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 111494971,1-Dimethyl-4-oxopiperidin-1-ium iodideHCID 450801402-(Pyrimidin-5-yl)propan-2-amine

Product 1

HCID 214715951-(2-(5-Pyrimidinyl)-prop-2-yl)-4-oxopiperidineYield 34.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 2-(5-pyrimidinyl)-2-propylamine (660 mg), ethanol (9 mL) and K2CO3 (665 mg) heated to reflux was added dropwise over 30 min, a solution of 1,1-dimethyl-4-oxopiperidinium iodide (1.9 g) in water (36 mL). When the addition was complete, the mixture was heated under reflux for an additional 2 h, cooled, basified to pH 10 with Na2CO3 and extracted with ethyl acetate (3 .Yen.100 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Column chromatography over silica gel, eluting with a methylene chloride; 5% methanol gave 360 mg of 1-(2-(5-pyrimidinyl)-prop-2-yl)-4-oxopiperidine as an oil: 1H NMR (400 MHz, CDCl3) 9.13 (s, 1H), 8.95 (s, 2H), 2.79 (t, 4H), 2.44 (t, 4H), 1.47 (s, 6H).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. additionwas added dropwise over 30 min
  4. additionWhen the addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for an additional 2 h
  7. temperaturecooled
  8. extractionextracted with ethyl acetate (3 .Yen.100 mL)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. washColumn chromatography over silica gel, eluting with a methylene chloride

Sources & evidence

ORD record
ord-2be575fc1c034a92b43d4da955ac96e3
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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