Potassium Carbonate → HCID 67176455, compound

HRID 1914623Notes

Reaction equation

HRID 1914623 reaction equation
Cl.[N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[NH2:8].C(=O)([O-])[O-].[K+].[K+].[N:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][C:23](OCC)=[O:24])=[N:17][CH:16]=1>C(O)C>[N:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:8]=[C:3]3[CH2:4][CH2:5][CH2:6][CH2:7][N:2]3[C:23](=[O:24])[CH:22]=2)=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852362-Iminopiperidine hydrochlorideHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate

Product 1

HCID 67176455HCID 67176455, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 25.0 g (185.72 mmol) of 3,4,5,6-tetrahydro-pyridin-2-ylamine monohydrochloride in 138 mL of ethanol was added 25.67 g (185.72 mmol) of potassium carbonate. The reaction mixture was stirred at room temperature for 10 min, 36.06 g (185.72 mmol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate was added and the resulting mixture was stirred under reflux for 16 h. The cooled solution was evaporated to remove solvent. The mixture was dissolved in ethylacetate, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The resulting solid was triturated in diethyl ether, filtrated to afford 9.23 g (22%) of the desired compound as a white-brown powder.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder reflux for 16 h
  3. customThe cooled solution was evaporated
  4. customto remove solvent
  5. dissolutionThe mixture was dissolved in ethylacetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customThe resulting solid was triturated in diethyl ether
  10. filtrationfiltrated

Sources & evidence

ORD record
ord-9880d80c0df540e5b7abb462b76a149f
Source dataset
uspto-grants-2013_12
Patent number
US08614219B2

Reaction notes

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