HCID 19020587, compound → 1-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975343Notes

Reaction equation

HRID 1975343 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 19020587HCID 19020587, compound

Product 1

HCID 189463571-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazineYield 87.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

37.2 g of 1-(4-nitrobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine are reduced at room temperature in 370 ml of tetrahydrofuran in the presence of 20 g of Raney nickel. The filtered reaction solution is concentrated by evaporation and the resulting oil is crystallised from isopropanol/petroleum ether, yielding 30 g of 1-(4-aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 111°-112°.

Workup

  1. customThe filtered reaction solution
  2. concentrationis concentrated by evaporation
  3. customthe resulting oil is crystallised from isopropanol/petroleum ether

Sources & evidence

ORD record
ord-788c09c380c14357b10a53bccc2e60ec
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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