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

HRID 433911노트

반응식

HRID 433911 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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 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+).

후처리

  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 was washed with methylene chloride (40 mL)
  10. temperatureThe aqueous phase was cooled
  11. filtrationthe precipitate was filtered
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-7df3b44caee94d2189561243862bc143
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670359B2

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