Acetic Acid → 4-(4-benzylpiperazin-1-yl)benzoic Acid

HRID 1017613Notes

Reaction equation

HRID 1017613 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:21]=[CH:20]C(C#N)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:23]([OH:26])(=[O:25])[CH3:24]>>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:21]=[CH:20][C:24]([C:23]([OH:26])=[O:25])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 80326914-(4-Benzylpiperazin-1-yl)benzonitrile

Product 1

HCID 47417244-(4-benzylpiperazin-1-yl)benzoic AcidYield 38%

Conditions

Temperature
100 °C

Procedure

4-(4-Benzylpiperazin-1-yl)benzonitrile (4.0 g, 15 mmol) was dissolved in glacial acetic acid (40 mL), 6 M hydrochloric acid (50 mL) was added and the reaction mixture was stirred at 100° C. for 17 h. The solvent was evaporated, the residue was suspended in water (10 mL) and the pH was adjusted to 3 by addition of 2 M sodium hydroxide (35 ml). The slurry was stirred at 50° C. for 2 h, cooled and the precipitate was filtered and dried in vacuo to give 4.1 g of a crude product. The solid was partitioned between methylene chloride (40 mL) and water (220 mL) with 2 M sodium hydroxide (8 mL). The aqueous phase wag washed with methylene chloride (40 mL) and the pH was adjusted to 5 with 2 M hydrochloric acid. The aqueous phase was cooled, the precipitate was filtered and dried in vacuo to give 1.6 g (38% yield) of the title compound: mp 226° C. (dec); EIMS (70 eV) m/z (relative intensity) 296 (44, M30 ).

Workup

  1. customThe solvent was evaporated
  2. additionthe pH was adjusted to 3 by addition of 2 M sodium hydroxide (35 ml)
  3. stirringThe slurry was stirred at 50° C. for 2 h
  4. temperaturecooled
  5. filtrationthe precipitate was filtered
  6. customdried in vacuo
  7. customto give 4.1 g of a crude product
  8. customThe solid was partitioned between methylene chloride (40 mL) and water (220 mL) with 2 M sodium hydroxide (8 mL)
  9. washThe aqueous phase wag washed with methylene chloride (40 mL)
  10. temperatureThe aqueous phase was cooled
  11. filtrationthe precipitate was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-6aba9a7af81841a78f1a82899e220eb0
Source dataset
uspto-grants-2002_11
Patent number
US06479497B1

Reaction notes

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