Water → Ethyl 4-(piperazin-1-yl)benzoate

HRID 1750728Notes

Reaction equation

HRID 1750728 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1)[CH3:8].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:1]1([C:14]2[CH:15]=[CH:16][C:11]([C:10]([O:9][CH2:7][CH3:8])=[O:18])=[CH:12][CH:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of piperazine (129.2 g, 1.5 mol), ethyl-4-fluorobenzoate (84 g, 0.5 mol), and potassium carbonate (103.65 g, 0.75 mol) in DMSO (200 mL) was stirred at 120° C. under N2 for six hours. The reaction mixture was then cooled to room temperature, poured into water (800 mL), and stirred for 30 minutes. The desired product was collected by filtration and carried to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringstirred for 30 minutes
  3. filtrationThe desired product was collected by filtration
  4. customcarried to the next step without further purification

Sources & evidence

ORD record
ord-bb45d72ed22549b79da0656ab77dfac3
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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