1-(2-Methoxyphenyl)piperazine → 1-(4-Bromo-2-methoxyphenyl)piperazine

HRID 2384938Notes

Reaction equation

HRID 2384938 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Br:15]Br>ClCCl>[Br:15][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 24408Bromine

Product 1

HCID 689488831-(4-Bromo-2-methoxyphenyl)piperazineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-(2-methoxy-phenyl)-piperazine (5.0 g, 26.0 mmol) in dichloromethane 450 mL) and cool to 0° C. Add bromine (4.16 g, 26.0 mmol) slowly dropwise. After 2 h wash the reaction mixture with 1 N sodium hydroxide (250 mL). Separate the organic portion, dry (Na2SO4), filter and concentrate in vacuo to afford 7.0 g (99%) of the title compound. MS/ES m/z (81Br) 273.0 [M+H]+.

Workup

  1. washAfter 2 h wash the reaction mixture with 1 N sodium hydroxide (250 mL)
  2. customSeparate the organic portion
  3. dry with materialdry (Na2SO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d0ea6e9fcfc041f58f2edcb5616a2142
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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