Sodium Bicarbonate → 4-(4-(4-Pyridyl)piperazin-1-yl)phenol

HRID 1493590Notes

Reaction equation

HRID 1493590 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 149869024-[4-(4-Pyridyl)piperazin-1-yl]anisole

Product 1

HCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of the product of part (i) (0.7 g, 2.6 mmole) and 48% hydrobromic acid (10 ml) was heated under reflux under a nitrogen atmosphere overnight. The hydrobromic acid was removed by concentration under reduced pressure, the residue dissolved in water and the solution obtained was basified with aqueous sodium bicarbonate solution. The resulting precipitate was removed by filtration and washed with methylene chloride to yield the desired product, m.p. 275°-276° (0.276 g, 41%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under a nitrogen atmosphere overnight
  3. customThe hydrobromic acid was removed by concentration under reduced pressure
  4. dissolutionthe residue dissolved in water
  5. customthe solution obtained
  6. customThe resulting precipitate was removed by filtration
  7. washwashed with methylene chloride

Sources & evidence

ORD record
ord-02d45e9e42714fb0aa59b04e8681b701
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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