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

HRID 640999

Reaction equation

HRID 640999 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
65 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-07b8551954aa446ba8517d6fd8f02df7
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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