Diethylcarbamoyl chloride → HCID 13313382, compound

HRID 543479Notes

Reaction equation

HRID 543479 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:18]([N:20]([CH2:24][CH3:25])[C:21](Cl)=[O:22])[CH3:19]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:13][CH2:14][N:15]([C:21](=[O:22])[N:20]([CH2:24][CH3:25])[CH2:18][CH3:19])[CH2:16][CH2:17]2)=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 13313382HCID 13313382, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 90 ml of chloroform was dissolved 3.6 g (0.0152 mole) of 1-(4-ethoxycarbonylphenyl)piperazine at room temperature. The temperature was elevated at 50° C. and a solution of 1.54 g (0.0114 mole) of diethylcarbamoyl chloride in 45 ml of chloroform was dropped to the above solution over a period of 30 minutes. The mixture was heated and refluxed for 2 hours, and the insoluble substance was removed and the filtrate was subjected to distillation under reduced pressure. The residue was mixed with 50 ml of a 35% aqueous solution of sodium hydroxide, and 200 ml of toluene was added and the mixture was stirred at room temperature for 30 minutes. The water layer was removed, and the organic layer was dried with anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was mixed with 20 ml of benzene and the mixture was stirred for a certain time. The benzene-insoluble substance was removed and the filtrate was subjected to silica gel chromatography to obtain 3.6 g of 1-(4-ethoxycarbonylphenyl)-4-diethylcarbamoylpiperazine having a melting point of 77° to 82° C.

Workup

  1. customwas elevated at 50° C.
  2. temperatureThe mixture was heated
  3. temperaturerefluxed for 2 hours
  4. customthe insoluble substance was removed
  5. distillationthe filtrate was subjected to distillation under reduced pressure
  6. additionThe residue was mixed with 50 ml of a 35% aqueous solution of sodium hydroxide, and 200 ml of toluene
  7. additionwas added
  8. customThe water layer was removed
  9. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  10. customthe solvent was removed by distillation under reduced pressure
  11. additionThe residue was mixed with 20 ml of benzene
  12. stirringthe mixture was stirred for a certain time
  13. customThe benzene-insoluble substance was removed

Sources & evidence

ORD record
ord-c00257b80a0b4ee2a06601655374d6b8
Source dataset
uspto-grants-1984_05
Patent number
US04446133

Reaction notes

Loading…