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

HRID 640999

反応式

HRID 640999 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 167921071-(4-Aminophenyl)piperidin-4-ol収率 51%

試薬・触媒・溶媒 1

HCID 935Nickel触媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-07b8551954aa446ba8517d6fd8f02df7
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

関連ノート

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