Potassium Carbonate → HCID 14878742, compound

HRID 1090060Notes

Reaction equation

HRID 1090060 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. The mixture was allowed to return to room temperature and was stirred for 75 minutes. The inorganic salts were filtered off and after 180 ml of N,N-diethylamine and 76 g of potassium carbonate were added to the filtrate, the mixture was refluxed for 75 minutes. The inorganic salts were filtered off after cooling and the filtrate was evaporated to dryness under reduced pressure. The 166.9 g of 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. additionafter 180 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. filtrationThe inorganic salts were filtered off
  6. temperatureafter cooling
  7. customthe filtrate was evaporated to dryness under reduced pressure
  8. customThe 166.9 g of residue were crystallized from 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-184c3f3eb5cf4c42b2c2b41c7117b039
Source dataset
uspto-grants-1992_01
Patent number
US05081113

Reaction notes

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