3,4-Dinitrophenol → HCID 57637399, compound

HRID 2078711Notes

Reaction equation

HRID 2078711 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].Cl.Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:13][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 113483,4-DinitrophenolHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 1

HCID 57637399HCID 57637399, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 3,4-dinitrophenol (2 g, 10.9 mmol, 1 eq) in dimethyl formamide (40 ml), chloropropyl piperidine hydrochloride (2.8 g, 14.2 mmol, 1.3 eq) and potassium carbonate (3.2 g, 22.9 mmol, 2.1 eq) were added. The mixture was heated to 100° C. for 4 hours and the reaction was cooled to room temperature. The mixture was passed through a SCX column and eluted with 7N ammonia in methanol, the eluent was concentrated and the residue was subjected to chromatography on silica gel (100 g) to yield 1-[3-(3,4-dinitro-phenoxy)-propyl]-piperidine [3.45 g] as a yellow oil.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. washeluted with 7N ammonia in methanol
  3. concentrationthe eluent was concentrated

Sources & evidence

ORD record
ord-93e04cf7649c43b6a22a0d541c299f78
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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