Morpholine → 4-(3-Nitrobenzyl)morpholine

HRID 2095202Notes

Reaction equation

HRID 2095202 reaction equation
Br[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.C(N(CC)CC)C>C1COCC1>[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

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 7832314-(3-Nitrobenzyl)morpholineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromomethyl-3-nitrobenzene (2.16 g, 10 mmol), morpholine (1.76 g, 20.2 mmol) and triethylamine (1.0 mL) in THF (60 mL) was heated for two hours at 60° C. The solvent was evaporated, water was added and the product was isolated by extraction with ether. The ether extract was dried over Mg2SO4 and the solvent was evaporated. The crystalline residue was used in the next step without further purification. The product, 4-(3-nitrobenzyl)morpholine, was obtained in 94% yield (2.09 g).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. customthe product was isolated by extraction with ether
  4. extractionThe ether extract
  5. dry with materialwas dried over Mg2SO4
  6. customthe solvent was evaporated
  7. customThe crystalline residue was used in the next step without further purification

Sources & evidence

ORD record
ord-ae695d3bf0e647c48f1a1e3ce3092256
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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