3,4-Dinitrophenol → 2-(3,4-Dinitro-phenoxy)-ethyl-morpholine

HRID 2064694Notes

Reaction equation

HRID 2064694 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][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]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][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 113483,4-DinitrophenolHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 224776912-(3,4-Dinitro-phenoxy)-ethyl-morpholineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-dinitrophenol (250 mg), 4-(2-chloroethyl)morpholine hydrochloride (252 mg) and potassium carbonate (375 mg) in dimethylformamide (3 ml) was heated at 120° C. for 20 minutes in a Personal Chemistry Smith Creator microwave. The reaction mixture was partitioned between ethyl acetate and water and the organic layer dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to give 4-[2-(3,4-dinitro-phenoxy)-ethyl]-morpholine (319 mg) as a yellow oil. LC-MS (METHOD B): RT=2.13 minutes, 298 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic layer dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-22f8f98cdbe44dbf958a00c107061a5d
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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