Methylamine → N-Methyl-1-(4-phenoxyphenyl)methanamine

HRID 1781138Notes

Reaction equation

HRID 1781138 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][NH2:17].C(OCC)(=O)C>CO.[Pd]>[CH3:16][NH:17][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 661394-Phenoxybenzaldehyde

Product 1

HCID 10608640N-Methyl-1-(4-phenoxyphenyl)methanamineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (10.0 g, 0.05 mol), excess methylamine and 1.5 g of 10% Pd/C in 200 mL of methanol were stirred under an atmosphere of hydrogen for 16 hours. After removal of the catalyst by filtration through Celite®, the filtrate was concentrated under reduced pressure to give the crude product as an oil. Chromatography on silica gel eluting with ethyl acetate gave the title compound in 80% yield.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration through Celite®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give the crude product as an oil

Sources & evidence

ORD record
ord-9172f8c663b2415390d899a38b676f70
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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