Sodium Bicarbonate → 4-(4-Phenethylpiperazin-1-yl)phenol

HRID 269869Notes

Reaction equation

HRID 269869 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>ClCCCl.B(Br)(Br)Br>[CH2:15]([N:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH2:14][CH2:13]1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 155270761-(4-Methoxyphenyl)-4-phenethylpiperazine

Product 1

HCID 231114454-(4-Phenethylpiperazin-1-yl)phenolYield 17.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of 1-(4-methoxyphenyl)-4-phenethylpiperazine (165 mg) in 1,2-dichloroethane (1.5 mL), boron tribromide (132 μL) was added under cooling with ice. The temperature was raised to the ambient level, followed by 3 hours' stirring. The reaction mixture was poured in saturated saline solution, rendered weakly alkaline with saturated aqueous sodium hydrogencarbonate solution, and the product was extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. Distilling the solvent off, the crude product recovered was purified on TLC (developer, chloroform: methanol=15:1) to provide 4-(4-phenethylpiperazin-1-yl)phenol (28 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe temperature was raised to the ambient level
  3. additionThe reaction mixture was poured in saturated saline solution
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationDistilling the solvent off, the crude product
  8. customrecovered
  9. customwas purified on TLC (developer, chloroform: methanol=15:1)

Sources & evidence

ORD record
ord-fd0340410c88452b8dd4913aae4ba310
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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