Dichloroacetyl chloride → ST50911991

HRID 905138

Reaction equation

HRID 905138 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 2837846ST50911991Yield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.1 g (0.048 mol) of dichloroacetyl chloride were added dropwise to a solution of 10 g (0.048 mol) of 1-(4-nitrophenyl)-piperazine and 5 g (0.495 mol) of triethylamine in 100 ml of toluene at room temperature, while stirring. The mixture was subsequently stirred at 20° C. for 3 hours. Working up was then effected by a procedure in which the reaction mixture was washed twice with 100 ml of water each time and the organic phase was separated off, dried and evaporated under reduced pressure. The residue was recrystallized from toluene. 7 g (46% of theory) of 1-(4-nitrophenyl)-4-dichloroacetyl-piperazine were obtained in the form of light yellow crystals of melting point 155° C.

Workup

  1. stirringThe mixture was subsequently stirred at 20° C. for 3 hours
  2. washwas washed twice with 100 ml of water each time
  3. customthe organic phase was separated off
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-a2ca27a80e8c43d2b6bf33d8d91bd5aa
Source dataset
uspto-grants-1983_12
Patent number
US04422866

Linked notes

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