Diethylcarbamoyl chloride → HCID 13042078, compound

HRID 543481Notes

Reaction equation

HRID 543481 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:16]([N:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH3:17]>C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([C:19](=[O:20])[N:18]([CH2:22][CH3:23])[CH2:16][CH3:17])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 97269Piperazin-4-ylacetophenone

Product 1

HCID 13042078HCID 13042078, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 50 ml of chloroform was dissolved 10.2 g (0.05 mole) of 1-(4-acetylphenyl)-piperazine at room temperature, and 6.8 g (0.05 mole) of diethylcarbamoyl chloride was dropped to the solution over a period of 30 minutes. The mixture was stirred at room temperature for 5 hours, and the insoluble substance was removed. The filtrate was subjected to distillation under reduced pressure and the residue was made alkaline by 4 N aqueous solution of sodium hydroxide and extracted with 100 ml of toluene. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was recrystallized from a benzene-hexane mixed solvent to obtain 1-(4-acetylphenyl)-4-diethylcarbamoylpiperazine having a boiling point of 72° to 76° C. The so obtained free base was dissolved in chloroform, and the solution was saturated with gaseous hydrogen chloride and stirred for a certain time. Then, the solution was subjected to a post treatment according to customary procedures to obtain 8.6 g of 1-(4-acetylphenyl)-4-diethylcarbamoylpiperazine hydrochloride having a melting point of 145° to 152° C.

Workup

  1. customthe insoluble substance was removed
  2. distillationThe filtrate was subjected to distillation under reduced pressure
  3. extractionextracted with 100 ml of toluene
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was recrystallized from a benzene-hexane mixed solvent

Sources & evidence

ORD record
ord-58ab6f9b968f465ca8729d48c07c8604
Source dataset
uspto-grants-1984_05
Patent number
US04446133

Reaction notes

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