Hydrazine hydrate (1:1) → N~1~-[3-(4-Methylpiperazin-1-yl)propyl]benzene-1,4-diamine

HRID 640983

반응식

HRID 640983 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.O.NN>[Ni].CCO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:6][CH2:7]1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

생성물 1

HCID 21975027N~1~-[3-(4-Methylpiperazin-1-yl)propyl]benzene-1,4-diamine수율 83.2%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

반응 조건

온도
65 °C

실험 절차

A 50 mL round bottom flask was charged with [3-(4-Methyl-piperazin-1-yl)-propyl]-(4-nitro-phenyl)-amine (as prepared in step 1 above; 0.365 g, 1.31 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.286 mL, 9.17 mmol) was then added to the solution. Excess RaNi was then added in dropwise until gas evolution from the solution ceased. The suspension was then allowed to stir for an additional 45 minutes at 65° C. The suspension was cooled to room temperature and then filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo affording pure N-[3-(4-Methyl-piperazin-1-yl)-propyl]-benzene-1,4-diamine as a light brown oil (0.269 g, 1.09 mmol, 83% yield).

후처리

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationfiltered over celite
  3. washThe celite was washed with MeOH (˜20 mL)
  4. concentrationthe combined organic solutions were then concentrated in vacuo

출처 및 근거

ORD 기록
ord-f4db72c518da41a68aadc7968f1f62c7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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