Imidazole → 1-(5-Imidazol-1-yl-2-nitro-phenyl)-piperidine

HRID 32890

Reaction equation

HRID 32890 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[OH-].[K+].O>CS(C)=O>[N:17]1([C:2]2[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:7]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 14797Potassium HydroxideHCID 30960791-(5-Chloro-2-nitrophenyl)piperidine

Product 1

HCID 693102461-(5-Imidazol-1-yl-2-nitro-phenyl)-piperidineYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To 1-(5-chloro-2-nitro-phenyl)-piperidine (184 mg, 0.760 mmol, as prepared in Example 3, step (a)) and imidazole (67.8 mg, 0.99 mmol) in 3 mL of DMSO was added KOH (64 mg, 1.1 mmol). The reaction was heated to 90° C. overnight. The dark solution was poured into 40 mL of water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo to give 190 mg (92%) of the title compound as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C14H16N4O2, 273.1 (M+H), found 273.1.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic layers were washed with water (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad354599bdf04ffcb22584abdfc98fe5
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Linked notes

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