Morpholine → 4-(4-Nitrophenyl)morpholine

HRID 1796314Notes

Reaction equation

HRID 1796314 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CC(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 8471TriethylamineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 252224-(4-Nitrophenyl)morpholineYield 103.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-Fluoro-4-nitrobenzene (3.00 mL, 28.3 mmol) was combined in a flask with anhydrous 2-propanol (28 mL), triethylamine (4.34 mL, 311 mmol), and morpholine (2.47 mL, 28.3 mmol). The mixture was refluxed for 3.5 h before adding additional morpholine (2.47 mL, 28.3 mmol) and refluxing for 20 h. The mixture was then cooled and concentrated under reduced pressure. Purification by silica gel flash chromatography provided 161-a (6.09 g, 98%) as a 95% pure solid. MS: APCI (AP−): 207.1 (M)−.

Workup

  1. temperatureThe mixture was refluxed for 3.5 h
  2. temperaturerefluxing for 20 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-d630c376f7e2413c86f0b24375ce0c80
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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