Water → 1-[(2,5-Dichlorophenyl)methyl]piperazine

HRID 2184833Notes

Reaction equation

HRID 2184833 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8](C(OCC)=O)[CH2:7][CH2:6]1.O.CCOC(C)=O.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22458123Ethyl 4-(2,5-dichlorobenzyl)piperazine-1-carboxylate

Product 1

HCID 46433681-[(2,5-Dichlorophenyl)methyl]piperazineYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution containing 13 g of 1-(2,5-dichlorobenzyl)-4-ethoxycarbonylpiperazine in 35 mL of 37% HCl was stirred for 40 h at reflux. Subsequently, 30 mL of water and 30 mL of EtOAc were added at room temperature, adjusting the pH to 11 via addition of 35% NaOH. The organic phase, which was dried on anhydrous sodium sulphate, was evaporated to dryness under vacuum. The crude was purified via flash chromatography (CHCl3-MeOH 7:3) giving 4.46 g (50%) of the title compound.

Workup

  1. temperatureat reflux
  2. dry with materialThe organic phase, which was dried on anhydrous sodium sulphate
  3. customwas evaporated to dryness under vacuum
  4. customThe crude was purified via flash chromatography (CHCl3-MeOH 7:3)

Sources & evidence

ORD record
ord-1dd7c67e968a4bd5929469251247f67a
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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