Triethylamine → HCID 54257295, compound

HRID 325985Notes

Reaction equation

HRID 325985 reaction equation
[N:1]1([C:6]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:22]([O:24][C:25]([O:27][C:28]1[CH:38]=[CH:37][C:31]([CH:32]=[CH:33][C:34](Cl)=[O:35])=[CH:30][CH:29]=1)=[O:26])[CH3:23]>C(Cl)(Cl)Cl>[CH2:22]([O:24][C:25]([O:27][C:28]1[CH:29]=[CH:30][C:31]([CH:32]=[CH:33][C:34]([N:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[O:7])[CH2:14][CH2:13]2)=[O:35])=[CH:37][CH:38]=1)=[O:26])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1006141-((Pyrrolidine-1-carbonyl)methyl)piperazineHCID 540500384-(3-Chloro-3-oxoprop-1-en-1-yl)phenyl ethyl carbonate

Product 1

HCID 54257295HCID 54257295, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 140 ml of chloroform were dissolved 17.7 g of 1-(pyrrolidinocarbonylmethyl)piperazine and 8.4 ml of triethylamine. To the solution was added 15.2 g of 4-(ethoxycarbonyloxy)cinnamoylchloride with ice-cooling, followed by stirring the resultant mixture overnight at room temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and dissolved in ethyl acetate. Any insoluble matter was removed by filtration, and the filtrate was extracted with 140 ml of 1N-hydrochloric acid. The extract was washed with ethyl acetate, neutralized with sodium bicarbonate and then extracted with chloroform. The chloroform layer was successively washed with water and then with brine. The layer was then dried and subjected to distillation to remove the solvent. The resultant crystals were recrystallized from ethyl acetate, thereby obtaining 13.4 g (yield: 54.0%) of 1-[4-(ethoxycarbonyloxy)cinnamoyl]-4-(pyrrolidinocarbonylmethyl)piperazine as crystals having a melting point of 128°-130° C.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. customAny insoluble matter was removed by filtration
  6. extractionthe filtrate was extracted with 140 ml of 1N-hydrochloric acid
  7. washThe extract was washed with ethyl acetate
  8. extractionextracted with chloroform
  9. washThe chloroform layer was successively washed with water
  10. customThe layer was then dried
  11. distillationsubjected to distillation
  12. customto remove the solvent
  13. customThe resultant crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9127c3b3b1a24a7aa72ab9b46ae60975
Source dataset
uspto-grants-1984_04
Patent number
US04443603

Reaction notes

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