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

HRID 857909Notes

Reaction equation

HRID 857909 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 80.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 4-(3-nitrobenzyl)morpholine (1.0 g, Reference Example 33) in ethanol (25 mL) was treated with 5% Pd/C (15 mg), then placed under a blanket of hydrogen. After stirring at room temperature for a further 2 hours the reaction mixture was filtered through celite and then evaporated. The residue was subjected to column chromatography on silica eluting with ethyl acetate to give the title compound (700 mg) as a light brown oil, Rf 0.08 (ethyl acetate). 1H NMR [(CDCl3]: δ 7.09 (t, 1H), 6.73–6.67 (m, 2H), 6.58 (d, 1H), 3.84–3.45 (t and bs overlapping, 6H), 3.41 (s, 2H) and 2.45 (t, 4H).

Workup

  1. filtrationwas filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-bbf4a3c405bd47339248770cae82759a
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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