Water → 1-(4-Nitrophenyl)-4-piperidinol

HRID 538007Notes

Reaction equation

HRID 538007 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.O>CN(C)C(=O)C>[OH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 6137681-(4-Nitrophenyl)-4-piperidinol

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

4-chloronitrobenzene (31.5 g, 200 mmol) was dissolved in N,N-dimethylacetamide (80 ml), and potassium carbonate (35.9 g, 260 mmol) and 4-hydroxypiperidine (22.3 g, 220 mmol) were added thereto, followed by stirring under heat at 130° C. for 3 hours. After cooling to room temperature, water was added to the mixture, and the precipitate was collected by filtration. The obtained solid was dried under reduced pressure, thereby obtaining 4-hydroxy-N-(4-nitrophenyl)piperidine (41.3 g, 93%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-a99eedc521d646f19e481d8770458f23
Source dataset
uspto-grants-2014_10
Patent number
US08865714B2

Reaction notes

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