4-(3-Nitrobenzyl)morpholine → 3-(Morpholin-4-ylmethyl)aniline

HRID 2086079Notes

Reaction equation

HRID 2086079 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O.[H][H]>C(O)C.[Pd]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 7832314-(3-Nitrobenzyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 10964063-(Morpholin-4-ylmethyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(3-nitrobenzyl)morpholine (3.0 g, 14 mmol) in ethanol (40 ml) was treated with 10% palladium on charcoal (150 mg) and hydrogenated at 50 psi until hydrogen uptake ceased (ca. 2 hours). The mixture was filtered through a glass microfibre filter paper (Whatman GF/A) and evaporated to dryness to give 3-(morpholin-4-ylmethyl)phenylamine as a colourless oil (2.6 g, 100%) which was used without purification. m/z (ES+) 193 (M++H).

Workup

  1. custom(ca. 2 hours)
  2. filtrationThe mixture was filtered through a glass microfibre
  3. filtrationfilter paper (Whatman GF/A)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a553040c6fb548b09431add3ca8ebacd
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

Loading…