Piperazine → HCID 57454346, compound

HRID 2232410Notes

Reaction equation

HRID 2232410 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][NH2:11])=[O:9])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N:12]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][NH2:11])=[O:9])[CH:3]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 72711Picolinic acid, 4-chloro-, hydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 57454346HCID 57454346, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-chloropyridine-2-carboxylic acid hydrazide (9.37 g), piperazine (20.0 g) and sodium bicarbonate (15 g) in n-butanol (120 ml) was heated under reflux with stirring for 18 hours and then cooled and filtered. The filtrate was evaporated and the residue was chromatographed on silica gel. Elution with a mixture of chloroform, ethanol and concentrated aqueous ammonia solution (50:50:1) gave the product as a solid (8.10 g), m.p. 212°-217° C. (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed on silica gel
  7. washElution
  8. additionwith a mixture of chloroform, ethanol and concentrated aqueous ammonia solution (50:50:1)

Sources & evidence

ORD record
ord-bfc33a4dba9a48778baea05266360479
Source dataset
uspto-grants-1988_11
Patent number
US04788196

Reaction notes

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