Diethylcarbamoyl chloride → HCID 422755, compound

HRID 543476Notes

Reaction equation

HRID 543476 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:14]([N:16]([CH2:20][CH3:21])[C:17](Cl)=[O:18])[CH3:15]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:17](=[O:18])[N:16]([CH2:20][CH3:21])[CH2:14][CH3:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 974781-(4-Chlorophenyl)piperazine

Product 1

HCID 422755HCID 422755, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 40 ml of methylene chloride was dissolved 4.0 g (0.02 mole) of 1-(4-chlorophenyl)piperazine at room temperature. Then, a solution of 3.0 g (0.022 mole) of diethylcarbamoyl chloride in 30 ml off methylene chloride was dropped to the above solution over a period of 30 minutes and the mixture was stirred for 4 hours at room temperature. The precipitate was removed and the filtrate was made alkaline by addition of 30 ml of a 35% aqueous solution of sodium hydroxide and extracted with 50 ml of methylene chloride. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure to obtain crude 1-(4-chlorophenyl)-4-diethylcarbamylpiperazine as the residue. The low-boiling-point component was removed by distillation under reduced pressure and the residue was recrystallized from n-hexane to obtain 1.8 g of a purified product having a melting point of 63° to 64° C. The yield was 29.9%. The elementary analysis values are as follows.

Workup

  1. customThe precipitate was removed
  2. additionby addition of 30 ml of a 35% aqueous solution of sodium hydroxide
  3. extractionextracted with 50 ml of methylene chloride
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customto obtain crude 1-(4-chlorophenyl)-4-diethylcarbamylpiperazine as the residue
  7. customThe low-boiling-point component was removed by distillation under reduced pressure
  8. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-bc7b48f22bfb4df4a73451729d0e6c9a
Source dataset
uspto-grants-1984_05
Patent number
US04446133

Reaction notes

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