3-Chloropropionyl chloride → 1-[4-(3-Chloropropionylamino)benzoyl]-4-[2-(4-chlorophenyl)-ethyl]piperazine

HRID 1975356Notes

Reaction equation

HRID 1975356 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.CCN(C(C)C)C(C)C.[Cl:34][CH2:35][CH2:36][C:37](Cl)=[O:38]>O1CCCC1>[Cl:34][CH2:35][CH2:36][C:37]([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:38]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 81531DiisopropylethylamineHCID 189463571-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 190994691-[4-(3-Chloropropionylamino)benzoyl]-4-[2-(4-chlorophenyl)-ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g of 1-(4-aminobenzoyl)-4-[2-(4-chlorophenyl)-ethyl]piperazine and 0.82 g of Hunig base are introduced into 40 ml of tetrahydrofuran, and a solution of 0.8 g of 3-chloropropionic acid chloride is added dropwise thereto. The solution is left to stand overnight. The resulting suspension is concentrated by evaporation and taken up in methylene chloride and water. There is obtained from the organic phase 1-[4-(3-chloropropionylamino)benzoyl]-4-[2-(4-chlorophenyl)-ethyl]piperazine having a melting point of 190°-191°.

Workup

  1. waitThe solution is left
  2. concentrationThe resulting suspension is concentrated by evaporation

Sources & evidence

ORD record
ord-028e8471258b4354948ce02202245b03
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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