Potassium Carbonate → HCID 14878742, compound

HRID 1463975Notes

Reaction equation

HRID 1463975 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13](Cl)[N:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([N:4]([CH2:5][CH3:6])[CH2:1][CH3:2])[N:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 837951-AcetylpiperazineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 14878742HCID 14878742, compoundYield 136.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 51.22 g of N-acetylpiperazine in 200 ml of acetonitrile was added over 50 minutes at 0° C. to a mixture of 78 g of 2,6-dichloro-3-nitropyridine, 600 ml of acetonitrile and 66.3 g of potassium carbonate and after the mixture was allowed to return to room temperature, it was stirred for 75 minutes. The inorganic salts were filtered off and 180 ml of N,N-diethylamine and 76 g of potassium carbonate were added to the filtrate. The mixture was refluxed for 75 minutes and after cooling, the inorganic salts were filtered off. The filtrate was evaporated to dryness under reduced pressure and the 166.9 g residue were crystallized from 200 ml of ethyl acetate to obtain 87.4 g of the expected product melting at 120° C.

Workup

  1. customto return to room temperature
  2. filtrationThe inorganic salts were filtered off
  3. addition180 ml of N,N-diethylamine and 76 g of potassium carbonate were added to the filtrate
  4. temperatureThe mixture was refluxed for 75 minutes
  5. temperatureafter cooling
  6. filtrationthe inorganic salts were filtered off
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. customthe 166.9 g residue were crystallized from 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-c2d371c460dd419c8b1f828c3730b958
Source dataset
uspto-grants-1994_04
Patent number
US05302719

Reaction notes

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