1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

HRID 1835084Notes

Reaction equation

HRID 1835084 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[OH-].[Na+].Br[CH2:19][CH2:20][Cl:21].C(OCC)(=O)C.ClCCl>CS(C)=O>[Cl:21][CH2:20][CH2:19][N:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineYield 54.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine HCl (52.5 mmol) and powdered sodium hydroxide (105 mmol) in DMSO (40 mL), was stirred at ambient temperature. After 0.5 h, 1-bromo-2-chloroethane (78.8 mmol) was added to the solution and left to stir for 4 h. The reaction was monitored by TLC (ethyl acetate: dichloromethane 1:4), upon completion, the mixture was poured into 200 mL of ice water and the product was extracted with dichloromethane twice, dried with sodium sulfate, and solvent was removed under vacuum. Flash chromatography (ethyl acetate: dichloromethane, 1:5 yielded an oil of the title compound (7.30 g).

Workup

  1. waitleft
  2. stirringto stir for 4 h
  3. extractionthe product was extracted with dichloromethane twice
  4. dry with materialdried with sodium sulfate, and solvent
  5. customwas removed under vacuum

Sources & evidence

ORD record
ord-36e46df3a27e462cb506585f3b8339fb
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

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