Morpholine → HCID 57629503, compound

HRID 2108362Notes

Reaction equation

HRID 2108362 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].[C:15](=[O:18])([O-])[O-].[K+].[K+].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(#N)C>[O:24]1[CH2:25][CH2:26][N:21]([C:9]2[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH:10]=2)[O:4][CH2:3][CH2:2][N:21]2[CH2:26][CH2:15][O:18][CH2:23][CH2:22]2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 24688592HCID 24688592, compound

Product 1

HCID 57629503HCID 57629503, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(2-bromoethoxy)-4-fluoro-1-nitrobenzene (160 mg, 0.6 mmol) in 20 mL acetonitrile under a nitrogen atmosphere was treated with potassium carbonate (360 mg, 2.6 mmol) and morpholine (0.3 mL, 3.4 mmol). The reaction mixture was heated to 70° C. for three hours and then filtered and concentrated. The residue was purified by flash chromatography (SiO2, 100% ethyl acetate/hexane) to give 4-(2-(5-morpholino-2-nitrophenoxy)ethyl)morpholine (50 mg, 25%). 1HNMR (CDCl3) δ 7.99 (m, 1H), 6.45 (m, 1H), 6.35 (s, 1H), 4.21 (t, 2H, J=4.0 Hz), 3.85 (t, 4H, J=4.0 Hz), 3.72 (t, 4H, J=4.0 Hz), 3.33 (t, 4H, J=4.0 Hz), 2.89 (t, 2H, J=4.0 Hz), 2.63 (t, 4H, J=4.0 Hz).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (SiO2, 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-490ad157e31341f29bd31858214d946e
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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