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

HRID 1074520Notes

Reaction equation

HRID 1074520 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.[OH2:15]>C(#N)C>[Cl:1][CH:2]([Cl:6])[C:3]([N:9]1[CH2:10][CH:11]([CH3:14])[N:12]([C:3](=[O:15])[CH:2]([Cl:6])[Cl:1])[CH2:13][CH:8]1[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6593Dichloroacetyl chlorideHCID 78162,5-Dimethylpiperazine

Product 1

HCID 1571521,1'-(2,5-Dimethylpiperazine-1,4-diyl)bis(2,2-dichloroethan-1-one)Yield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 acetonitrile at 20° C., while stirring. The reaction mixture was allowed to react subsequently at 20° C. for 5 hours and was then poured into 300 ml of water and the precipitate obtained was filtered off and recrystallized from toluene. 12 g (36% of theory) of N,N'-bis-(dichloroacetyl)-2,5-dimethylpiperazine were obtained in this manner in the form of colorless crystals of melting point 214° C.

Workup

  1. customto react subsequently at 20° C. for 5 hours
  2. customthe precipitate obtained
  3. filtrationwas filtered off
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-1c7950f7e0c94ff6bd5cdc3f7f1263bd
Source dataset
uspto-grants-1983_07
Patent number
US04392882

Reaction notes

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