Hydrazine hydrate (1:1) → N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine

HRID 640989노트

반응식

HRID 640989 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Ni].CCO>[N:13]1([CH2:12][CH2:11][NH:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 585989084-Nitro-N-[2-(pyrrolidin-1-yl)ethyl]aniline

생성물 1

HCID 16090620N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine수율 71.3%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

반응 조건

온도
65 °C

실험 절차

A 25 mL round bottom flask was charged with (4-Nitro-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine (0.352 g, 1.50 mmol mmol) and EtOH (5 mL). Hydrazine Hydrate (0.326 mL, 10.5 mmol) was then added to the solution. Excess RaNi was then added in dropwise until gas evolution ceased. The suspension was then allowed to stir for an additional 1 h at 65° C. The suspension was cooled to room temperature and then was filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo affording pure N-(2-Pyrrolidin-1-yl-ethyl)-benzene-1,4-diamine as a light purple oil (0.219 g, 1.07 mmol, 71% yield).

후처리

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationwas filtered 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-2f65560b35624e60b901a5e11da990d8
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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