4-(4-Nitrobenzyl)morpholine → 4-(Morpholinomethyl)aniline

HRID 1387769Notes

Reaction equation

HRID 1387769 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Product 1

HCID 7768514-(Morpholinomethyl)anilineYield 1.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (300 ml) was dissolved 4-(4-nitrobenzyl)morpholine (25.8 g), and to the mixture was added dried 10% palladium on carbon (Pd—C) (1.00 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 20 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was separated and purified with column chromatography (ethyl acetate) to give 4-(4-aminobenzyl)morpholine (430 mg) as pale yellow crystals.

Workup

  1. additionto the mixture was added
  2. dry with materialdried 10% palladium on carbon (Pd—C) (1.00 g)
  3. filtrationThe palladium was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-098e4c0e8763481fbb31b5b13e6d9731
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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