Morpholine → 4-(4-Nitrophenyl)morpholine

HRID 2217597Notes

Reaction equation

HRID 2217597 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, 31.1 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-21fb27ca004942c584584afde94fdb8b
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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