Methylamine → N-methyl-2-methoxy-3,4-methylenedioxybenzylamine

HRID 622199Notes

Reaction equation

HRID 622199 reaction equation
[CH3:1][O:2][C:3]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:14][NH2:15]>CO.[Pd]>[CH3:14][NH:15][CH2:5][C:4]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][O:11][C:10]=2[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-

Product 1

HCID 21294019N-methyl-2-methoxy-3,4-methylenedioxybenzylamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.0 g of 2-methoxy-3,4-methylenedioxybenzaldehyde was suspended in 30 ml of methanol, to which 4.31 g of 40% methylamine aqueous solution (2 equivalent) was added. 59 mg of 5% Pd/C catalyst (0.1 mol %) was added to the obtained reaction mixture and hydrogenation was carried out at ordinary temperature and atmospheric pressure. Absorption of hydrogen was completed in about 2 hours to quantitatively obtain N-methylbenzylamine derivative. The catalyst was filtered out and excessive methylamine, water formed and methanol solvent were distilled off to obtain an oily N-methyl-2-methoxy-3,4-methylenedioxybenzylamine. (Yield 100%).

Workup

  1. additionwas added
  2. customAbsorption of hydrogen
  3. filtrationThe catalyst was filtered out and excessive methylamine, water
  4. customformed
  5. distillationmethanol solvent were distilled off

Sources & evidence

ORD record
ord-04d48ad4b86e4108894843fda42f493e
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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