Ethanol → 1-(4-Aminophenyl)piperidin-4-ol

HRID 640999

반응식

HRID 640999 반응식
CN1CCN([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)CC1.[OH2:21].NN.[CH3:24][CH2:25]O>[Ni]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([N:11]2[CH2:10][CH2:9][CH:8]([OH:21])[CH2:25][CH2:24]2)=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

생성물 1

HCID 167921071-(4-Aminophenyl)piperidin-4-ol수율 51%

시약·촉매·용매 1

HCID 935Nickel촉매

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 (0.742 g, 3.34 mmol) and dissolved into EtOH (20 mL). Hydrazine Hydrate (0.642 mL, 20.04 mmol) was then added. Excess RaNi was then added in dropwise until the solution stopped bubbling. The suspension was then allowed to stir for an additional 15 minutes at 65° C. The suspension was cooled to rt and then filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo. The crude oil was then purified over silica (3% Chloroform/Hexanes to 10% Chloroform/Hexanes) affording pure 1-(4-amino-phenyl)-piperidin-4-ol as a light brown oil in 51% yield (0.327 g, 1.71 mmol).

후처리

  1. customstopped bubbling
  2. temperatureThe suspension was cooled to rt
  3. filtrationfiltered over celite
  4. washThe celite was washed with MeOH (˜20 mL)
  5. concentrationthe combined organic solutions were then concentrated in vacuo
  6. customThe crude oil was then purified over silica (3% Chloroform/Hexanes to 10% Chloroform/Hexanes)

출처 및 근거

ORD 기록
ord-07b8551954aa446ba8517d6fd8f02df7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

연결된 노트

불러오는 중…