Diethylcarbamoyl chloride → HCID 423348, compound

HRID 543474Notes

Reaction equation

HRID 543474 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([N:15]([CH2:19][CH3:20])[C:16](Cl)=[O:17])[CH3:14]>C(Cl)(Cl)Cl>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:16](=[O:17])[N:15]([CH2:19][CH3:20])[CH2:13][CH3:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 70961-Phenylpiperazine

Product 1

HCID 423348HCID 423348, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
40 °C

Procedure

In 70 ml of chloroform was dissolved 12.0 g (0.074 mole) of 1-phenylpiperazine at room temperature, and a solution of 10.9 g (0.08 mole) of diethylcarbamoyl chloride in 30 ml of chloroform was dropped to the above solution over a period of 30 minutes. Then, the mixture was stirred at 40° C. for 5 hours and then cooled. The precipitated white crystal was removed, and the filtrate was concentrated under reduced pressure and 50 ml of a 25% aqueous solution of sodium hydroxide was added. The mixture was extracted 2 times with 50 ml of benzene and dried with anhydrous sodium sulfate. The solvent was removed by distillation to obtain crude 1-phenyl-4-diethylcarbamoylpiperazine as the residue. By distillation under reduced pressure, 5.7 g of a purified product having a boiling point of 180.5° C. at 2.3 mm Hg was obtained. The yield was 29.5%. The elementary analysis values are as follows.

Workup

  1. temperaturecooled
  2. customThe precipitated white crystal was removed
  3. concentrationthe filtrate was concentrated under reduced pressure and 50 ml of a 25% aqueous solution of sodium hydroxide
  4. additionwas added
  5. extractionThe mixture was extracted 2 times with 50 ml of benzene
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-416a86444ddd4642a190750fe848741f
Source dataset
uspto-grants-1984_05
Patent number
US04446133

Reaction notes

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