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

HRID 2187464Notes

Reaction equation

HRID 2187464 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
50 °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 mL9 nd water (220 mL) with 2 M sodium hydroxide (8 mL). The aqueous phase was 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, M+).

Workup

  1. customThe solvent was evaporated
  2. additionthe pH was adjusted to 3 by addition of 2 M sodium hydroxide (35 ml)
  3. temperaturecooled
  4. filtrationthe precipitate was filtered
  5. customdried in vacuo
  6. customto give 4.1 g of a crude product
  7. customThe solid was partitioned between methylene chloride (40 mL9 nd water (220 mL) with 2 M sodium hydroxide (8 mL)
  8. washThe aqueous phase was washed with methylene chloride (40 mL)
  9. temperatureThe aqueous phase was cooled
  10. filtrationthe precipitate was filtered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-347e6e94bdbf470ab75433cab1c42a57
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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