Acetone → HCID 12901337, compound

HRID 1065517Notes

Reaction equation

HRID 1065517 reaction equation
CC(C)=O.[F:5][C:6]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]([OH:12])[NH:10][C:9](=[O:13])[NH:8][C:7]1=O.C(OC(=O)C)(=O)C.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>N1C=CC=CC=1>[F:5][C:6]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[NH:8][C:9](=[O:13])[NH:10][C:11]1=[O:12]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 8082PiperidineHCID 12901279HCID 12901279, compound

Product 1

HCID 12901337HCID 12901337, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml. of acetone is dissolved 4.40 g. of ethyl 5-fluoro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxo-pyrimidine-5-carboxylate, followed by the addition of 2.5 ml. of acetic anhydride. To this is further added dropwise 2 ml. of pyridine and the mixture is allowed to stand at room temperature for 24 hours. To the colorless reaction mixture thus obtained is added dropwise 5.9 ml. of piperidine, whereby the reaction takes place with evolution of heat. After 5.5 hours' standing at room temperature, volatiles are distilled off under reduced pressure and the yellow oily residue is dissolved in chloroform. The solution is subjected to column chromatography on silica gel (80 g., solvent:chloroform). The fractions rich in the desired compound are concentrated under reduced pressure to recover 5.20 g. of a white solid. Upon recrystallization from chloroform-hexane, 3.0 g. of ethyl 5-fluoro-6-piperidino-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate is obtained as colorless needles.

Workup

  1. additionTo this is further added dropwise 2 ml
  2. customTo the colorless reaction mixture thus obtained
  3. additionis added dropwise 5.9 ml
  4. temperatureof heat
  5. waitAfter 5.5 hours' standing at room temperature
  6. distillationvolatiles are distilled off under reduced pressure
  7. dissolutionthe yellow oily residue is dissolved in chloroform
  8. concentrationThe fractions rich in the desired compound are concentrated under reduced pressure
  9. customto recover 5.20 g
  10. customUpon recrystallization from chloroform-hexane, 3.0 g

Sources & evidence

ORD record
ord-ca6dfab6485745dba958dcf5aa4ba3ad
Source dataset
uspto-grants-1982_05
Patent number
US04329460

Reaction notes

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