Potassium Carbonate → 1-[4-(3-Ethoxypropylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975346Notes

Reaction equation

HRID 1975346 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.[CH2:25]([O:27][CH2:28][CH2:29][CH2:30]Br)[CH3:26].C([O-])([O-])=O.[K+].[K+]>C(O)(C)C>[CH2:25]([O:27][CH2:28][CH2:29][CH2:30][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)[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2604931-bromo-3-ethoxypropaneHCID 189463571-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 190994271-[4-(3-Ethoxypropylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

11 g of 1-(4-aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine and 5.7 g of 3-ethoxypropyl bromide are suspended in 150 ml of isopropanol and dissolved at 100°. 9.4 g of potash are added thereto, and the mixture is boiled under reflux for 20 hours. Concentration by evaporation and chromatography over silica gel yield an oil, which is crystallised from methylene chloride and petroleum ether, yielding 1-[4-(3-ethoxypropylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 87°-89°.

Workup

  1. dissolutiondissolved at 100°
  2. temperatureunder reflux for 20 hours
  3. concentrationConcentration
  4. customby evaporation and chromatography over silica gel
  5. customyield an oil, which
  6. customis crystallised from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-8e0152fa8b7a4eda9ce8432ef410d20a
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

Loading…