4-Hydroxybenzoic Acid → 1-[(3-Chlorophenyl)phenylmethyl]piperazine

HRID 565740Notes

Reaction equation

HRID 565740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:9]2[CH2:14][CH2:13][N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(C(O)=O)=CC=1.N>Br.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 222AmmoniaHCID 22111520(+)-1-[(3-Chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine

Product 1

HCID 45645251-[(3-Chlorophenyl)phenylmethyl]piperazine

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

(+)-1-[(3-Chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine (4.62 g, 10.48 mmol) was stirred in 30% hydrobromic acid-acetic acid solution (20 ml) in the presence of 4-hydroxybenzoic acid (5.06g, 36.66 mmol) at room temperature for two days. 28%-Aqueous ammonia was added to the reaction mixture, and the resulting mixture was extracted with chloroform. The chloroform layer was washed with water and then dried over anhydrous magnesium sulfate. Thereafter, the crude product obtained by removing the solvent by evaporation in vacuo was purified by column chromatography on silica gel with chloroform-methanol (20:1), to give

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-baec8aeef9964a438d1d53f4cda5789c
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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