1-Bromo-2-Chloroethane → 1-(2-chloroethyl)-4-(3-chlorophenyl)piperazine

HRID 1835082Notes

Reaction equation

HRID 1835082 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Br[CH2:18][CH2:19][Cl:20]>CS(C)=O>[Cl:20][CH2:19][CH2:18][N:12]1[CH2:13][CH2:14][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 256811-(3-Chlorophenyl)piperazine monohydrochloride

Product 1

HCID 100154081-(2-chloroethyl)-4-(3-chlorophenyl)piperazineYield 59.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (3-chloro-phenyl)-piperazine hydrochloride (51.5 mmol) and powdered sodium hydroxide (103 mmol) in DMSO (75 mL) was treated with 2-bromo-1-chloroethane (77.2 mmol) and stirred at ambient temperature for 4 h. The reaction was poured into ice cold water (200 mL) and stirred for 0.5 h. A solid mass formed and was separated by decanting the water. The aqueous layer was extracted with dichloromethane (100 mL). The solid mass was dissolved with dichloromethane (100 mL) and the combined organics were dried with sodium sulfate, filtered and the solvent removed under vacuum. Flash chromatography (chloroform:acetone 50:1 to 20:1) yielded an oil (7.95 g) as the titled compound.

Workup

  1. stirringstirred for 0.5 h
  2. customA solid mass formed
  3. customwas separated
  4. customby decanting the water
  5. extractionThe aqueous layer was extracted with dichloromethane (100 mL)
  6. dissolutionThe solid mass was dissolved with dichloromethane (100 mL)
  7. dry with materialthe combined organics were dried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-4ebb85a8e21b49908b44bbb6e47b5bb2
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

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