1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazine

HRID 1907829Notes

Reaction equation

HRID 1907829 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[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:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 936011-(3,4-Dichlorophenyl)piperazine

Product 1

HCID 120698951-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazineYield 36.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (3,4-dichlorophenyl)piperazine (500 mg) and powdered sodium hydroxide (87 mg) in DMSO (5 mL) was treated with 2-bromo-1-chloroethane (387 mg) and stirred at ambient temperature for 16 hours. The reaction was poured into ice cold water (15 mL) and stirred for 0.5 hours. A solid mass formed and was separated by decanting the water. The aqueous layer was extracted with dichloromethane (5 mL). The solid mass was dissolved with dichloromethane (5 mL) and the combined organics were dried with sodium sulfate, filtered and the solvent removed under vacuum. Flash chromatography (dichloromethane:methanol 1:0 to 10:1) yielded an oil (230 mg) as the titled compound.

Workup

  1. stirringstirred for 0.5 hours
  2. customA solid mass formed
  3. customwas separated
  4. customby decanting the water
  5. extractionThe aqueous layer was extracted with dichloromethane (5 mL)
  6. dissolutionThe solid mass was dissolved with dichloromethane (5 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-b4462ccafec74b5bb474c18f6dc4c928
Source dataset
uspto-grants-2013_12
Patent number
US08598180B2

Reaction notes

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