Morpholine → 4-(3-Nitrobenzyl)morpholine

HRID 880623Notes

Reaction equation

HRID 880623 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12078alpha-Chloro-m-nitrotoluene

Product 1

HCID 7832314-(3-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL, one-neck, round bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1-chloromethyl-3-nitrobenzene (10.0 g, 58.3 mmol), morpholine (15.0 g, 175 mmol) and toluene (75 mL), and the solution was heated at reflux for 2.5 h. The reaction mixture was allowed to cool to ambient temperature then washed with 1N aqueous sodium hydroxide (2×50 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL), and the combined extracts were dried over sodium sulfate and concentrated under reduced pressure to afford compound 9 as an off-white solid. 1H NMR (CDCl3) δ (ppm) 8.22 (s, 1H), 8.12 (d, 1H, J=8.2 Hz), 7.68 (d, 1H, J=7.6 Hz), 7.49 (t, 1H, J=7.9 Hz), 3.73 (m, 4H), 3.59 (s, 2H), 2.46 (m, 4H).

Workup

  1. customA 250 mL, one-neck, round bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperaturethe solution was heated
  4. temperatureat reflux for 2.5 h
  5. washthen washed with 1N aqueous sodium hydroxide (2×50 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  7. dry with materialthe combined extracts were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1f9e6a37b59481db720572ad51fe201
Source dataset
uspto-grants-2015_03
Patent number
US08993583B2

Reaction notes

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