Sodium Hydroxide → 1-(4-Bromo-3-methoxyphenyl)piperazine

HRID 353456

Reaction equation

HRID 353456 reaction equation
[BrH:1].Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+]>CS(C)=O>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 235137561-(3-Methoxyphenyl)piperazine dihydrobromide

Product 1

HCID 210710161-(4-Bromo-3-methoxyphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1-(3-methoxyphenyl)piperazine dihydrobromide (3.5 g, 10 mmol) is dissolved in DMSO (30 mL) and heated at 65° C. for 4 h in a flask which is open to the atmosphere. After cooling, the mixture is poured into a separatory funnel containing 100 mL of 1 N sodium hydroxide solution and extracted with ethyl ether (3×100 mL). The organic extracts are dried (Na2SO4), filtered, and concentrated to provide 1-(4-bromo-3-methoxyphenyl)piperazine as a solid. 1H NMR (400 MHz, CDCl3) 7.34-7.36 (d, J=2.2 Hz, 1H,), 6.47 (s, 1H), 6.38-6.41 (d, J=2.8 Hz, 1H), 3.87 (s, 3H, OMe), 3.11-3.13 (m, 4H), 3.01-3.03 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured into a separatory funnel
  3. extractionextracted with ethyl ether (3×100 mL)
  4. dry with materialThe organic extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53cdd144b05545e280f07cb8705d705a
Source dataset
uspto-grants-2004_06
Patent number
US06753336B2

Linked notes

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