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

HRID 131141ノート

反応式

HRID 131141 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-6812eec9b55a4fdab265f877e30d3eba
出典データセット
uspto-grants-2008_06
特許番号
US07384943B2

反応ノート

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