Chloroacetyl chloride → 1-(4-Chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975347Notes

Reaction equation

HRID 1975347 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:32][CH2:33][C:34]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:23][CH:24]=1)=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 189463571-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 189463301-(4-Chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.7 g of 1-(4-aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine and 0.55 g of triethylamine are introduced into 25 ml of methylene chloride. A solution of 0.6 g of chloroacetyl chloride is added dropwise thereto. The dark solution is left to stand overnight, diluted with 50 ml of methylene chloride, washed with 1N sodium hydroxide solution, dried over magnesium sulfate and concentrated by evaporation. The crystallisate so obtained is recrystallised from acetone, yielding 1-(4-chloroacetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 146°-147°.

Workup

  1. waitThe dark solution is left
  2. washwashed with 1N sodium hydroxide solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe crystallisate so obtained
  6. customis recrystallised from acetone

Sources & evidence

ORD record
ord-5f501aecbbe8401e9b882e4794ab9948
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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