Diethylcarbamoyl chloride → N,N-diethyl-4-(4-methoxyphenyl)piperazine-1-carboxamide

HRID 543477Notes

Reaction equation

HRID 543477 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:15]([N:17]([CH2:21][CH3:22])[C:18](Cl)=[O:19])[CH3:16]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:18](=[O:19])[N:17]([CH2:21][CH3:22])[CH2:15][CH3:16])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 422756N,N-diethyl-4-(4-methoxyphenyl)piperazine-1-carboxamideYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

In 75 ml of chloroform was dissolved 10.4 g (0.054 mole) of 1-(4-methoxyphenyl)piperazine at room temperature, and a solution of 7.4 g (0.054 mole) of diethylcarbamoyl chloride in 50 ml of chloroform was dropped to the above solution over a period of 30 minutes. The mixture was stirred at 50° C. for 2 hours, and the insoluble substance was removed, and the filtrate was concentrated under reduced pressure and 100 ml of a 35% aqueous solution of sodium hydroxide and 300 ml of ether were added to the concentrate. The mixture was stirred for a certain time, and the ether layer was dried with anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography and distillation under reduced pressure to obtain 7.4 of purified 1-(4-methoxyphenyl)-4-diethylcarbamoylpiperazine having a boiling point 195° C. at 0.5 mm Hg. The yield was 47.0%. Elementary analysis values are as follows.

Workup

  1. customthe insoluble substance was removed
  2. concentrationthe filtrate was concentrated under reduced pressure and 100 ml of a 35% aqueous solution of sodium hydroxide and 300 ml of ether
  3. additionwere added to the concentrate
  4. stirringThe mixture was stirred for a certain time
  5. dry with materialthe ether layer was dried with anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. distillationthe residue was purified by silica gel chromatography and distillation under reduced pressure

Sources & evidence

ORD record
ord-a9226e2efe664cc89ed309fa47fac3db
Source dataset
uspto-grants-1984_05
Patent number
US04446133

Reaction notes

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