Dichloroacetyl chloride → 1,1'-(2,5-Dimethylpiperazine-1,4-diyl)bis(2,2-dichloroethan-1-one)

HRID 1074519Notes

Reaction equation

HRID 1074519 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[CH3:7][CH:8]1[CH2:13][NH:12][CH:11]([CH3:14])[CH2:10][NH:9]1>C1(C)C=CC=CC=1>[Cl:1][CH:2]([Cl:6])[C:3]([N:9]1[CH2:10][CH:11]([CH3:14])[N:12]([C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])[CH2:13][CH:8]1[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 78162,5-Dimethylpiperazine

Product 1

HCID 1571521,1'-(2,5-Dimethylpiperazine-1,4-diyl)bis(2,2-dichloroethan-1-one)Yield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

29.4 g (0.2 mol) of dichloroacetyl chloride were added dropwise to a solution of 22.8 g (0.2 mol) of 2,5-dimethyl-piperazine in 150 ml of toluene at 20° C., while stirring. The mixture was subsequently stirred at 20° C. for 5 hours. Thereafter, the precipitate which had formed was filtered off and recrystallized twice from toluene. 8 g (24% of theory) of N,N'-bis-(dichloroacetyl)-2,5-dimethyl-piperazine were obtained in this manner in the form of colorless crystals of melting point 215° C.

Workup

  1. stirringThe mixture was subsequently stirred at 20° C. for 5 hours
  2. customThereafter, the precipitate which had formed
  3. filtrationwas filtered off
  4. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-d469e98b857249d483dda76d7ef2f232
Source dataset
uspto-grants-1983_07
Patent number
US04392882

Reaction notes

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