Methylamine → HCID 22241370, compound

HRID 892160Notes

Reaction equation

HRID 892160 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O.[CH3:16][NH2:17]>C1COCC1.[Pd]>[CH3:16][NH:17][CH2:11][C:10]1[CH:9]=[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 157551753-[(2-Methoxyethoxy)methoxy]benzaldehyde

Product 1

HCID 22241370HCID 22241370, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-methoxyethoxy-methoxy)-benzaldehyde (2.10 g, 10 mmol, example 8a) in THF (60 mL) is added methylamine (20 mL, 2M in THF) followed by palladium on carbon (210 mg, 10% Pd). The resulting mixture is stirred for 24 h under an atmosphere of hydrogen gas, then purged with nitrogen, filtered through celite and the filtrate concentrated. The residue is purified by flash chromatography (silica, 10% methanol in dichloromethane) to give the title compound as an oil.

Workup

  1. custompurged with nitrogen
  2. filtrationfiltered through celite
  3. concentrationthe filtrate concentrated
  4. customThe residue is purified by flash chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c7e97488af34174a56ab2518c500fe0
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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