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

HRID 2227798Notes

Reaction equation

HRID 2227798 reaction equation
CO[CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][Cl:24]>CN(C=O)C>[CH3:15][O:18][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:4]1[CH2:3][CH2:8][N:7]([CH2:22][CH2:23][Cl:24])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 20200458HCID 20200458, compound

Product 1

HCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, a solution of 19.2 g (0.1 mol) of o-methoxyphenylpiperazine and 13.8 g (0.1 mol) of potassium carbonate in 200 ml of DMF was initially charged and, after 30 min, 30 ml (0.36 mol) of 1-bromo-2-chloroethane were added. The mixture was stirred at room temperature for 2 h. The mixture was poured into ice-water then extracted with methyl tert-butyl ether, and the organic phases were washed with water, dried with sodium sulfate and subsequently concentrated. The residue was dissolved in ethyl acetate and the hydrochloride was precipitated out by addition of 30% strength isopropanol/HCI solution, filtered off with suction and dried at 40° C. in a vacuum drying oven. This gave 17 g (67%) of substance. Melting point 200° C.

Workup

  1. extractionthen extracted with methyl tert-butyl ether
  2. washthe organic phases were washed with water
  3. dry with materialdried with sodium sulfate
  4. concentrationsubsequently concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customthe hydrochloride was precipitated out by addition of 30% strength isopropanol/HCI solution
  7. filtrationfiltered off with suction
  8. customdried at 40° C. in a vacuum
  9. customdrying oven

Sources & evidence

ORD record
ord-854af58a8498481e9d058934a36b4e3f
Source dataset
uspto-grants-2002_07
Patent number
US06414157B1

Reaction notes

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