Acetic Acid → 2-Chloro-4-(4-methylpiperazin-1-yl)aniline

HRID 1262071

反応式

HRID 1262071 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O)(=O)C>[Fe].O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 231396071-(3-Chloro-4-nitrophenyl)-4-methylpiperazine

生成物 1

HCID 574160942-Chloro-4-(4-methylpiperazin-1-yl)aniline収率 25%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

1-(3-Chloro-4-nitro-phenyl)-4-methyl-piperazine (2.016 g, 7.885 mmol) was combined with Tetrahydrofuran (30 mL). The resulting mixture was filtered. The filtrate was combined with Acetic acid (40 mL, 700 mmol), then at room temperature Iron (2932 mg, 52.50 mmol) was added neat and the mixture was warmed to 35° C. under a nitrogen atmosphere. After 16 h filtered mixture and concentrated resulting filtrate under reduced pressure. The concentrated residue was partitioned between CHCl3 (2×) and saturated aqueous NaHCO3. Combined organics, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 0.44 g (25%) of 2-Chloro-4-(4-methyl-piperazin-1-yl)-phenylamine as a yellow tinted oil, which crystallized on sitting. This material was used without further manipulation for the subsequent step. LC/MS (E/I+) 226.05 (M+H).

後処理

  1. filtrationThe resulting mixture was filtered
  2. filtrationAfter 16 h filtered mixture
  3. concentrationconcentrated
  4. customresulting filtrate under reduced pressure
  5. customThe concentrated residue was partitioned between CHCl3 (2×) and saturated aqueous NaHCO3
  6. dry with materialCombined organics, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f20b74768544417ca913d27e5a2d0121
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

関連ノート

読み込み中…