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

HRID 1262071

반응식

HRID 1262071 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
35 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f20b74768544417ca913d27e5a2d0121
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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