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

HRID 1277016Notes

Reaction equation

HRID 1277016 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-fd1b12a463344deba61180b9cc849dc5
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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