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

HRID 649812Notes

Reaction equation

HRID 649812 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.C(OCC)(=O)C.[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 of 13 g of Compound 14A in 35 mL of 37% HCl was first stirred at reflux for a period of 40 hr, followed by the addition of 30 mL water and 30 mL ethyl acetate, with the pH level adjusted to 11 through addition of a suitable quantity of 35% NaOH. The obtained organic phase was then dried over anhydrous sodium sulphate, followed by evaporation under vacuum. The obtained crude product residue was then purified by flash chromatography (chloroform—methanol 7:3). By this means, 4.46 g of Compound 14B (yield 50%) was obtained.

Workup

  1. temperatureat reflux for a period of 40 hr
  2. dry with materialThe obtained organic phase was then dried over anhydrous sodium sulphate
  3. customfollowed by evaporation under vacuum
  4. customThe obtained crude product residue
  5. customwas then purified by flash chromatography (chloroform—methanol 7:3)

Sources & evidence

ORD record
ord-d01832000bfb4346897097acf3f0e862
Source dataset
uspto-grants-2001_08
Patent number
US06271234B1

Reaction notes

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