Acetic Acid → HCID 54398794, compound

HRID 2351949Notes

Reaction equation

HRID 2351949 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:12]1([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH3:20])=[O:19])[CH2:14][CH2:13]1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[CH:12]1([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH:20]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])=[O:19])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 14627908HCID 14627908, compound

Product 1

HCID 54398794HCID 54398794, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

o-Nitrobenzaldehyde (7.6 g, 0.05 mole) and acetoacetic cyclopropylamide (7.1 g, 0.05 mole) are dissolved in benzene (40 ml) and thereto are added piperidine (0.2 ml) and acetic acid (0.6 ml), and the mixture is refluxed for 2 hours and the produced water is removed. After the stoichiometic amount of water is distilled off, the reaction is stopped. After the reaction, the reaction mixture is washed with 5% hydrochloric acid and then with water, and the solvent is distilled off under reduced pressure, and to the residue is added diethyl ether, and the obtained crude crystals are recrystallized from ethanol to give the title compound (10.4 g, yield 75.6%) as colorless needles, m.p. 133°-134° C.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customthe produced water is removed
  3. distillationAfter the stoichiometic amount of water is distilled off
  4. customAfter the reaction
  5. washthe reaction mixture is washed with 5% hydrochloric acid
  6. distillationwith water, and the solvent is distilled off under reduced pressure
  7. additionto the residue is added diethyl ether
  8. customthe obtained crude crystals
  9. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-2014cf112da144f08d20489e2b7da7ed
Source dataset
uspto-grants-1989_10
Patent number
US04874773

Reaction notes

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