Morpholine → 4-[2-(4-Nitrophenyl)ethyl]morpholine

HRID 1989033Notes

Reaction equation

HRID 1989033 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromide

Product 1

HCID 27974734-[2-(4-Nitrophenyl)ethyl]morpholineYield 93.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-Bromo-ethyl)-4-nitro-benzene (1 g, 4.3 mmol) was added to a mixture of morpholine (435 μL, 5 mmol) and potassium carbonate (690 mg, 5.0 mmol) in 5 mL of DMSO. The mixture was stirred at 100° C. for 1 hour. After cooling to room temperature, the mixture was extracted into ethyl acetate (EtOAc), washed with water, brine and then dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with EtOAc/CH3OH/NH4OH (10:1:0.1, v/v), gave 950 mg of 4-[2-(4-nitro-phenyl)-ethyl]-morpholine, which was converted to the title compound under normal hydrogenation conditions. The title compound was obtained as a yellow solid (880 mg, 99%). 1H NMR (400 MHz, CDCl3) δ (ppm): 6.98 (d, J=8.2 Hz, 2H), 6.61 (d, J=8.2 Hz, 2H), 3.73 (t, J=4.5 Hz, 4H), 3.57 (br, 2H), 2.64-2.71 (m, 2H), 2.45-2.56 (m, 6H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted into ethyl acetate (EtOAc)
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulfate (Na2SO4)
  5. customRemoval of the solvent and chromatography on silica
  6. washeluting with EtOAc/CH3OH/NH4OH (10:1:0.1

Sources & evidence

ORD record
ord-7a2804bda97d43c089a9213fb450d847
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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