Potassium Hydroxide → 1-(2-Chloro-3-methylphenyl)piperazine

HRID 1084695Notes

Reaction equation

HRID 1084695 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br.Br[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Br.[OH-].[K+]>O>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 114124382-Chloro-m-toluidineHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 151240931-(2-Chloro-3-methylphenyl)piperazineYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 6.08 g of 2-chloro-3-methylaniline, 9 g of di(2-bromoethyl)amine hydrobromide and 4 ml of water was added a solution of 0.8 g of potassium hydorxide and 2.5 ml of water 3 times of 1 hour interval at 100° C., then the reaction mixture was stirred at the same temperature for 9 hours. To the resultant reaction mixture was added potassium hydroxide to make the mixture alkaline, and the mixture was extracted with diethyl ether, washed with water, dried with anhydrous magnesium sulfate. The solvent was removed by evaporation and the residue thus obtained was purified by means of a silica gel column chromatography (eluent: 5%-methanol/chloroform), and obtained 3.41 g of 4-(2-chloro-3-methylphenyl)piperazine.

Workup

  1. customTo the resultant reaction mixture
  2. extractionthe mixture was extracted with diethyl ether
  3. washwashed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe residue thus obtained
  7. customwas purified by means of a silica gel column chromatography (eluent: 5%-methanol/chloroform)

Sources & evidence

ORD record
ord-bddfb4fad3654e35b394208baaf54b01
Source dataset
uspto-grants-1991_04
Patent number
US05006528

Reaction notes

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