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

HRID 1796749Notes

Reaction equation

HRID 1796749 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CS(C)=O>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateYield 86.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl 4-fluorobenzoate (20.1 g) was dissolved in dimethyl sulfoxide (50 ml). Piperazine (31.1 g) was added to the solution, and the mixture was stirred at 120° C. for 2 hr. The reaction solution was poured into 1.2 liters of ice water. The precipitated crystal was washed with a mixed solution composed of hexane (500 ml) and diethyl ether (50 ml), was collected by filtration, and was dried under the reduced pressure to give 24.3 g (86.8%) of ethyl 4-(piperazin-1-yl)benzoate.

Workup

  1. washThe precipitated crystal was washed with a mixed solution
  2. filtrationwas collected by filtration
  3. customwas dried under the reduced pressure

Sources & evidence

ORD record
ord-b7d31fa6a451486e8745bfe8d300b787
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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